feat: implement agent caches and fix invalid prompt cache configs

- Added a new function `_warm_agent_jit_caches` to pre-warm agent caches at startup, reducing cold invocation costs.
- Updated the `SurfSenseContextSchema` to include per-invocation fields for better state management during agent execution.
- Introduced caching mechanisms in various tools to ensure fresh database sessions are used, improving performance and reliability.
- Enhanced middleware to support new context features and improve error handling during connector and document type discovery.

surfsense_backend/.env.example

@@ -324,3 +324,30 @@ LANGSMITH_PROJECT=surfsense
 # SURFSENSE_ENABLE_PLUGIN_LOADER=false
 # Comma-separated allowlist of plugin entry-point names
 # SURFSENSE_ALLOWED_PLUGINS=year_substituter
+
+# -----------------------------------------------------------------------------
+# Compiled-agent cache (Phase 1 + 2 perf optimization, default ON)
+# -----------------------------------------------------------------------------
+# When ON, the per-turn LangGraph + middleware compile result (~3-5s of CPU
+# on a cold turn) is reused across subsequent turns on the same thread,
+# collapsing it to a microsecond hash lookup. All connector tools acquire
+# their own short-lived DB session per call (Phase 2 refactor) so a cached
+# closure is safe to share across requests. Flip OFF only as a last-resort
+# rollback if you suspect cache-related staleness.
+# SURFSENSE_ENABLE_AGENT_CACHE=true
+
+# Cache capacity (max number of compiled-agent entries kept in memory)
+# and TTL per entry (seconds). Working set is typically one entry per
+# active thread on this replica; tune up for very large deployments.
+# SURFSENSE_AGENT_CACHE_MAXSIZE=256
+# SURFSENSE_AGENT_CACHE_TTL_SECONDS=1800
+
+# -----------------------------------------------------------------------------
+# Connector discovery TTL cache (Phase 1.4 perf optimization)
+# -----------------------------------------------------------------------------
+# Caches the per-search-space "available connectors" + "available document
+# types" lookups that ``create_surfsense_deep_agent`` hits on every turn.
+# ORM event listeners auto-invalidate on connector / document inserts,
+# updates and deletes — the TTL only bounds staleness for bulk-import
+# paths that bypass the ORM. Set to 0 to disable the cache.
+# SURFSENSE_CONNECTOR_DISCOVERY_TTL_SECONDS=30

surfsense_backend/app/agents/new_chat/agent_cache.py

@@ -0,0 +1,357 @@
+"""TTL-LRU cache for compiled SurfSense deep agents.
+
+Why this exists
+---------------
+
+``create_surfsense_deep_agent`` runs a 4-5 second pipeline on EVERY chat
+turn:
+
+1. Discover connectors & document types from Postgres (~50-200ms)
+2. Build the tool list (built-in + MCP) (~200ms-1.7s)
+3. Compose the system prompt
+4. Construct ~15 middleware instances (CPU)
+5. Eagerly compile the general-purpose subagent
+   (``SubAgentMiddleware.__init__`` calls ``create_agent`` synchronously,
+   which builds a second LangGraph + Pydantic schemas — ~1.5-2s of pure
+   CPU work)
+6. Compile the outer LangGraph
+
+For a single thread, all six steps produce the SAME object on every turn
+unless the user has changed their LLM config, toggled a feature flag,
+added a connector, etc. The right answer is to compile ONCE per
+"agent shape" and reuse the resulting :class:`CompiledStateGraph` for
+every subsequent turn on the same thread.
+
+Why a per-thread key (not a global pool)
+----------------------------------------
+
+Most middleware in the SurfSense stack captures per-thread state in
+``__init__`` closures (``thread_id``, ``user_id``, ``search_space_id``,
+``filesystem_mode``, ``mentioned_document_ids``). Cross-thread reuse
+would silently leak state across users and threads. Keying the cache on
+``(llm_config_id, thread_id, ...)`` gives us safe reuse for repeated
+turns on the same thread without changing any middleware's behavior.
+
+Phase 2 will move those captured fields onto :class:`SurfSenseContextSchema`
+(read via ``runtime.context``) so the cache can collapse to a single
+``(llm_config_id, search_space_id, ...)`` key shared across threads. Until
+then, per-thread keying is the only safe option.
+
+Cache shape
+-----------
+
+* TTL-LRU: entries auto-expire after ``ttl_seconds`` (default 1800s, 30
+  minutes — matches a typical chat session). ``maxsize`` (default 256)
+  caps memory; LRU evicts least-recently-used on overflow.
+* In-flight de-duplication: per-key :class:`asyncio.Lock` so concurrent
+  cold misses on the same key wait for the first build instead of
+  building N times.
+* Process-local: this is an in-memory cache. Multi-replica deployments
+  pay the build cost once per replica per key. That's fine; the working
+  set per replica is small (one entry per active thread on that replica).
+
+Telemetry
+---------
+
+Every lookup logs ``[agent_cache]`` lines through ``surfsense.perf``:
+
+  * ``hit`` — cache hit, microseconds-fast
+  * ``miss`` — first build for this key, includes build duration
+  * ``stale`` — entry was found but expired; rebuilt
+  * ``evict`` — LRU eviction (size-limited)
+  * ``size`` — current cache occupancy at lookup time
+"""
+
+from __future__ import annotations
+
+import asyncio
+import hashlib
+import logging
+import os
+import time
+from collections import OrderedDict
+from collections.abc import Awaitable, Callable
+from dataclasses import dataclass
+from typing import Any
+
+from app.utils.perf import get_perf_logger
+
+logger = logging.getLogger(__name__)
+_perf_log = get_perf_logger()
+
+
+# ---------------------------------------------------------------------------
+# Public API: signature helpers (cache key components)
+# ---------------------------------------------------------------------------
+
+
+def stable_hash(*parts: Any) -> str:
+    """Compute a deterministic SHA1 of the str repr of ``parts``.
+
+    Used for cache key components that need a fixed-width representation
+    (system prompt, tool list, etc.). SHA1 is fine here — this is not a
+    security boundary, just a content fingerprint.
+    """
+    h = hashlib.sha1(usedforsecurity=False)
+    for p in parts:
+        h.update(repr(p).encode("utf-8", errors="replace"))
+        h.update(b"\x1f")  # ASCII unit separator between parts
+    return h.hexdigest()
+
+
+def tools_signature(
+    tools: list[Any] | tuple[Any, ...],
+    *,
+    available_connectors: list[str] | None,
+    available_document_types: list[str] | None,
+) -> str:
+    """Hash the bound-tool surface for cache-key purposes.
+
+    The signature changes whenever:
+
+    * A tool is added or removed from the bound list (built-in toggles,
+      MCP tools loaded for the user changes, gating rules flip, etc.).
+    * The available connectors / document types for the search space
+      change (new connector added, last connector removed, new document
+      type indexed). Because :func:`get_connector_gated_tools` derives
+      ``modified_disabled_tools`` from ``available_connectors``, the
+      tool surface is technically already covered — but we hash the
+      connector list separately so an empty-list "no tools changed"
+      situation still rotates the key when, say, the user re-adds a
+      connector that gates a tool we were already not exposing.
+
+    Stays stable across:
+
+    * Process restarts (tool names + descriptions are static).
+    * Different replicas (everyone gets the same hash for the same
+      inputs).
+    """
+    tool_descriptors = sorted(
+        (getattr(t, "name", repr(t)), getattr(t, "description", "")) for t in tools
+    )
+    connectors = sorted(available_connectors or [])
+    doc_types = sorted(available_document_types or [])
+    return stable_hash(tool_descriptors, connectors, doc_types)
+
+
+def flags_signature(flags: Any) -> str:
+    """Hash the resolved :class:`AgentFeatureFlags` dataclass.
+
+    Frozen dataclasses are deterministically reprable, so a SHA1 of their
+    repr is a stable fingerprint. Restart safe (flags are read once at
+    process boot).
+    """
+    return stable_hash(repr(flags))
+
+
+def system_prompt_hash(system_prompt: str) -> str:
+    """Hash a system prompt string. Cheap, ~30µs for typical prompts."""
+    return hashlib.sha1(
+        system_prompt.encode("utf-8", errors="replace"),
+        usedforsecurity=False,
+    ).hexdigest()
+
+
+# ---------------------------------------------------------------------------
+# Cache implementation
+# ---------------------------------------------------------------------------
+
+
+@dataclass
+class _Entry:
+    value: Any
+    created_at: float
+    last_used_at: float
+
+
+class _AgentCache:
+    """In-process TTL-LRU cache with per-key in-flight de-duplication.
+
+    NOT THREAD-SAFE in the multithreading sense — designed for a single
+    asyncio event loop. Uvicorn runs one event loop per worker process,
+    so this is fine; multi-worker deployments simply each maintain their
+    own cache.
+    """
+
+    def __init__(self, *, maxsize: int, ttl_seconds: float) -> None:
+        self._maxsize = maxsize
+        self._ttl = ttl_seconds
+        self._entries: OrderedDict[str, _Entry] = OrderedDict()
+        # One lock per key — guards "build" so concurrent cold misses on
+        # the same key wait for the first build instead of all racing.
+        self._locks: dict[str, asyncio.Lock] = {}
+
+    def _now(self) -> float:
+        return time.monotonic()
+
+    def _is_fresh(self, entry: _Entry) -> bool:
+        return (self._now() - entry.created_at) < self._ttl
+
+    def _evict_if_full(self) -> None:
+        while len(self._entries) >= self._maxsize:
+            evicted_key, _ = self._entries.popitem(last=False)
+            self._locks.pop(evicted_key, None)
+            _perf_log.info(
+                "[agent_cache] evict key=%s reason=lru size=%d",
+                _short(evicted_key),
+                len(self._entries),
+            )
+
+    def _touch(self, key: str, entry: _Entry) -> None:
+        entry.last_used_at = self._now()
+        self._entries.move_to_end(key, last=True)
+
+    async def get_or_build(
+        self,
+        key: str,
+        *,
+        builder: Callable[[], Awaitable[Any]],
+    ) -> Any:
+        """Return the cached value for ``key`` or call ``builder()`` to make it.
+
+        ``builder`` MUST be idempotent — concurrent cold misses on the
+        same key collapse to a single ``builder()`` call (the others
+        wait on the in-flight lock and observe the populated entry on
+        wake).
+        """
+        # Fast path: hot hit.
+        entry = self._entries.get(key)
+        if entry is not None and self._is_fresh(entry):
+            self._touch(key, entry)
+            _perf_log.info(
+                "[agent_cache] hit key=%s age=%.1fs size=%d",
+                _short(key),
+                self._now() - entry.created_at,
+                len(self._entries),
+            )
+            return entry.value
+
+        # Stale entry — drop it; rebuild below.
+        if entry is not None and not self._is_fresh(entry):
+            _perf_log.info(
+                "[agent_cache] stale key=%s age=%.1fs ttl=%.0fs",
+                _short(key),
+                self._now() - entry.created_at,
+                self._ttl,
+            )
+            self._entries.pop(key, None)
+
+        # Slow path: serialize concurrent misses for the same key.
+        lock = self._locks.setdefault(key, asyncio.Lock())
+        async with lock:
+            # Double-check after acquiring the lock — another waiter may
+            # have populated the entry while we slept.
+            entry = self._entries.get(key)
+            if entry is not None and self._is_fresh(entry):
+                self._touch(key, entry)
+                _perf_log.info(
+                    "[agent_cache] hit key=%s age=%.1fs size=%d coalesced=true",
+                    _short(key),
+                    self._now() - entry.created_at,
+                    len(self._entries),
+                )
+                return entry.value
+
+            t0 = time.perf_counter()
+            try:
+                value = await builder()
+            except BaseException:
+                # Don't cache failed builds; let the next caller retry.
+                _perf_log.warning(
+                    "[agent_cache] build_failed key=%s elapsed=%.3fs",
+                    _short(key),
+                    time.perf_counter() - t0,
+                )
+                raise
+            elapsed = time.perf_counter() - t0
+
+            # Insert + evict.
+            self._evict_if_full()
+            now = self._now()
+            self._entries[key] = _Entry(value=value, created_at=now, last_used_at=now)
+            self._entries.move_to_end(key, last=True)
+            _perf_log.info(
+                "[agent_cache] miss key=%s build=%.3fs size=%d",
+                _short(key),
+                elapsed,
+                len(self._entries),
+            )
+            return value
+
+    def invalidate(self, key: str) -> bool:
+        """Drop a single entry; return True if anything was removed."""
+        removed = self._entries.pop(key, None) is not None
+        self._locks.pop(key, None)
+        if removed:
+            _perf_log.info(
+                "[agent_cache] invalidate key=%s size=%d",
+                _short(key),
+                len(self._entries),
+            )
+        return removed
+
+    def invalidate_prefix(self, prefix: str) -> int:
+        """Drop every entry whose key starts with ``prefix``. Returns count."""
+        keys = [k for k in self._entries if k.startswith(prefix)]
+        for k in keys:
+            self._entries.pop(k, None)
+            self._locks.pop(k, None)
+        if keys:
+            _perf_log.info(
+                "[agent_cache] invalidate_prefix prefix=%s removed=%d size=%d",
+                _short(prefix),
+                len(keys),
+                len(self._entries),
+            )
+        return len(keys)
+
+    def clear(self) -> None:
+        n = len(self._entries)
+        self._entries.clear()
+        self._locks.clear()
+        if n:
+            _perf_log.info("[agent_cache] clear removed=%d", n)
+
+    def stats(self) -> dict[str, Any]:
+        return {
+            "size": len(self._entries),
+            "maxsize": self._maxsize,
+            "ttl_seconds": self._ttl,
+        }
+
+
+def _short(key: str, n: int = 16) -> str:
+    """Truncate keys for log lines so they don't blow up log volume."""
+    return key if len(key) <= n else f"{key[:n]}..."
+
+
+# ---------------------------------------------------------------------------
+# Module-level singleton
+# ---------------------------------------------------------------------------
+
+_DEFAULT_MAXSIZE = int(os.getenv("SURFSENSE_AGENT_CACHE_MAXSIZE", "256"))
+_DEFAULT_TTL = float(os.getenv("SURFSENSE_AGENT_CACHE_TTL_SECONDS", "1800"))
+
+_cache: _AgentCache = _AgentCache(maxsize=_DEFAULT_MAXSIZE, ttl_seconds=_DEFAULT_TTL)
+
+
+def get_cache() -> _AgentCache:
+    """Return the process-wide compiled-agent cache singleton."""
+    return _cache
+
+
+def reload_for_tests(*, maxsize: int = 256, ttl_seconds: float = 1800.0) -> _AgentCache:
+    """Replace the singleton with a fresh cache. Tests only."""
+    global _cache
+    _cache = _AgentCache(maxsize=maxsize, ttl_seconds=ttl_seconds)
+    return _cache
+
+
+__all__ = [
+    "flags_signature",
+    "get_cache",
+    "reload_for_tests",
+    "stable_hash",
+    "system_prompt_hash",
+    "tools_signature",
+]

surfsense_backend/app/agents/new_chat/chat_deepagent.py

@@ -40,6 +40,13 @@ from langchain_core.tools import BaseTool
 from langgraph.types import Checkpointer
 from sqlalchemy.ext.asyncio import AsyncSession
 
+from app.agents.new_chat.agent_cache import (
+    flags_signature,
+    get_cache,
+    stable_hash,
+    system_prompt_hash,
+    tools_signature,
+)
 from app.agents.new_chat.context import SurfSenseContextSchema
 from app.agents.new_chat.feature_flags import AgentFeatureFlags, get_flags
 from app.agents.new_chat.filesystem_backends import build_backend_resolver
@@ -53,6 +60,7 @@ from app.agents.new_chat.middleware import (
     DedupHITLToolCallsMiddleware,
     DoomLoopMiddleware,
     FileIntentMiddleware,
+    FlattenSystemMessageMiddleware,
     KnowledgeBasePersistenceMiddleware,
     KnowledgePriorityMiddleware,
     KnowledgeTreeMiddleware,
@@ -330,23 +338,39 @@ async def create_surfsense_deep_agent(
         else None,
     )
 
-    # Discover available connectors and document types for this search space
+    # Discover available connectors and document types for this search space.
+    #
+    # NOTE: These two calls cannot be parallelized via ``asyncio.gather``.
+    # ``ConnectorService`` shares a single ``AsyncSession`` (``self.session``);
+    # SQLAlchemy explicitly forbids concurrent operations on the same session
+    # ("This session is provisioning a new connection; concurrent operations
+    # are not permitted on the same session"). The Phase 1.4 in-process TTL
+    # cache in ``connector_service`` already collapses the warm path to a
+    # near-zero pair of dict lookups, so sequential awaits cost nothing in
+    # the common case while remaining correct on cold cache misses.
     available_connectors: list[str] | None = None
     available_document_types: list[str] | None = None
 
     _t0 = time.perf_counter()
     try:
-        connector_types = await connector_service.get_available_connectors(
-            search_space_id
-        )
-        if connector_types:
-            available_connectors = _map_connectors_to_searchable_types(connector_types)
+        try:
+            connector_types_result = await connector_service.get_available_connectors(
+                search_space_id
+            )
+            if connector_types_result:
+                available_connectors = _map_connectors_to_searchable_types(
+                    connector_types_result
+                )
+        except Exception as e:
+            logging.warning("Failed to discover available connectors: %s", e)
 
-        available_document_types = await connector_service.get_available_document_types(
-            search_space_id
-        )
-
-    except Exception as e:
+        try:
+            available_document_types = (
+                await connector_service.get_available_document_types(search_space_id)
+            )
+        except Exception as e:
+            logging.warning("Failed to discover available document types: %s", e)
+    except Exception as e:  # pragma: no cover - defensive outer guard
         logging.warning(f"Failed to discover available connectors/document types: {e}")
     _perf_log.info(
         "[create_agent] Connector/doc-type discovery in %.3fs",
@@ -469,29 +493,77 @@ async def create_surfsense_deep_agent(
     # entire middleware build + main-graph compile into a single
     # ``asyncio.to_thread`` so the heavy CPU work runs off-loop and the
     # event loop stays responsive.
+    #
+    # PHASE 1: cache the resulting compiled graph. ``agent_cache`` is keyed
+    # on every per-request value that any middleware in the stack closes
+    # over in ``__init__`` — drop one and you risk leaking state across
+    # threads. Hits collapse this whole block to a microsecond lookup;
+    # misses pay the original CPU cost AND populate the cache.
+    config_id = agent_config.config_id if agent_config is not None else None
+
+    async def _build_agent() -> Any:
+        return await asyncio.to_thread(
+            _build_compiled_agent_blocking,
+            llm=llm,
+            tools=tools,
+            final_system_prompt=final_system_prompt,
+            backend_resolver=backend_resolver,
+            filesystem_mode=filesystem_selection.mode,
+            search_space_id=search_space_id,
+            user_id=user_id,
+            thread_id=thread_id,
+            visibility=visibility,
+            anon_session_id=anon_session_id,
+            available_connectors=available_connectors,
+            available_document_types=available_document_types,
+            # ``mentioned_document_ids`` is consumed by
+            # ``KnowledgePriorityMiddleware`` per turn via
+            # ``runtime.context`` (Phase 1.5). We still pass the
+            # caller-provided list here for the legacy fallback path
+            # (cache disabled / context not propagated) — the middleware
+            # drains its own copy after the first read so a cached graph
+            # never replays stale mentions.
+            mentioned_document_ids=mentioned_document_ids,
+            max_input_tokens=_max_input_tokens,
+            flags=_flags,
+            checkpointer=checkpointer,
+        )
+
     _t0 = time.perf_counter()
-    agent = await asyncio.to_thread(
-        _build_compiled_agent_blocking,
-        llm=llm,
-        tools=tools,
-        final_system_prompt=final_system_prompt,
-        backend_resolver=backend_resolver,
-        filesystem_mode=filesystem_selection.mode,
-        search_space_id=search_space_id,
-        user_id=user_id,
-        thread_id=thread_id,
-        visibility=visibility,
-        anon_session_id=anon_session_id,
-        available_connectors=available_connectors,
-        available_document_types=available_document_types,
-        mentioned_document_ids=mentioned_document_ids,
-        max_input_tokens=_max_input_tokens,
-        flags=_flags,
-        checkpointer=checkpointer,
-    )
+    if _flags.enable_agent_cache and not _flags.disable_new_agent_stack:
+        # Cache key components — order matters only for human readability;
+        # the resulting hash is what's stored. Every component must
+        # rotate on a real shape change AND stay stable across identical
+        # invocations.
+        cache_key = stable_hash(
+            "v1",  # schema version of the key — bump if components change
+            config_id,
+            thread_id,
+            user_id,
+            search_space_id,
+            visibility,
+            filesystem_selection.mode,
+            anon_session_id,
+            tools_signature(
+                tools,
+                available_connectors=available_connectors,
+                available_document_types=available_document_types,
+            ),
+            flags_signature(_flags),
+            system_prompt_hash(final_system_prompt),
+            _max_input_tokens,
+            # ``mentioned_document_ids`` deliberately omitted — middleware
+            # reads it from ``runtime.context`` (Phase 1.5).
+        )
+        agent = await get_cache().get_or_build(cache_key, builder=_build_agent)
+    else:
+        agent = await _build_agent()
     _perf_log.info(
-        "[create_agent] Middleware stack + graph compiled in %.3fs",
+        "[create_agent] Middleware stack + graph compiled in %.3fs (cache=%s)",
         time.perf_counter() - _t0,
+        "on"
+        if _flags.enable_agent_cache and not _flags.disable_new_agent_stack
+        else "off",
     )
 
     _perf_log.info(
@@ -1038,6 +1110,14 @@ def _build_compiled_agent_blocking(
         noop_mw,
         retry_mw,
         fallback_mw,
+        # Coalesce a multi-text-block system message into one block
+        # immediately before the model call. Sits innermost on the
+        # system-message-mutation chain so it observes every appender
+        # (todo / filesystem / skills / subagents …) and prevents
+        # OpenRouter→Anthropic from redistributing ``cache_control``
+        # across N blocks and tripping Anthropic's 4-breakpoint cap.
+        # See ``middleware/flatten_system.py`` for full rationale.
+        FlattenSystemMessageMiddleware(),
         # Tool-call repair must run after model emits but before
         # permission / dedup / doom-loop interpret the calls.
         repair_mw,

surfsense_backend/app/agents/new_chat/context.py

@@ -1,10 +1,25 @@
 """
 Context schema definitions for SurfSense agents.
 
-This module defines the custom state schema used by the SurfSense deep agent.
+This module defines the per-invocation context object passed to the SurfSense
+deep agent via ``agent.astream_events(..., context=ctx)`` (LangGraph >= 0.6).
+
+The agent's compiled graph is the same across invocations (and cached by
+``agent_cache``), so anything that varies per turn — the user mentions a
+specific document, the front-end issues a unique ``request_id``, etc. —
+MUST live on this context object instead of being captured into a
+middleware ``__init__`` closure. Middlewares read fields back via
+``runtime.context.<field>``; tools read them via ``runtime.context``.
+
+This object is read inside both ``KnowledgePriorityMiddleware`` (for
+``mentioned_document_ids``) and any future middleware that needs
+per-request state without invalidating the compiled-agent cache.
 """
 
-from typing import NotRequired, TypedDict
+from __future__ import annotations
+
+from dataclasses import dataclass, field
+from typing import TypedDict
 
 
 class FileOperationContractState(TypedDict):
@@ -15,25 +30,35 @@ class FileOperationContractState(TypedDict):
     turn_id: str
 
 
-class SurfSenseContextSchema(TypedDict):
+@dataclass
+class SurfSenseContextSchema:
     """
-    Custom state schema for the SurfSense deep agent.
+    Per-invocation context for the SurfSense deep agent.
 
-    This extends the default agent state with custom fields.
-    The default state already includes:
-    - messages: Conversation history
-    - todos: Task list from TodoListMiddleware
-    - files: Virtual filesystem from FilesystemMiddleware
+    Defaults are chosen so the dataclass can be safely default-constructed
+    (LangGraph's ``Runtime.context`` itself defaults to ``None`` if no
+    context is supplied — see ``langgraph.runtime.Runtime``). All fields
+    are optional; consumers must None-check before reading.
 
-    We're adding fields needed for knowledge base search:
-    - search_space_id: The user's search space ID
-    - db_session: Database session (injected at runtime)
-    - connector_service: Connector service instance (injected at runtime)
+    Phase 1.5 fields:
+        search_space_id: Search space the request is scoped to.
+        mentioned_document_ids: KB documents the user @-mentioned this turn.
+            Read by ``KnowledgePriorityMiddleware`` to seed its priority
+            list. Stays out of the compiled-agent cache key — that's the
+            whole point of putting it here.
+        file_operation_contract: One-shot file operation contract emitted
+            by ``FileIntentMiddleware`` for the upcoming turn.
+        turn_id / request_id: Correlation IDs surfaced by the streaming
+            task; populated for telemetry.
+
+    Phase 2 will extend with: thread_id, user_id, visibility,
+    filesystem_mode, anon_session_id, available_connectors,
+    available_document_types, created_by_id (everything currently captured
+    by middleware ``__init__`` closures).
     """
 
-    search_space_id: int
-    file_operation_contract: NotRequired[FileOperationContractState]
-    turn_id: NotRequired[str]
-    request_id: NotRequired[str]
-    # These are runtime-injected and won't be serialized
-    # db_session and connector_service are passed when invoking the agent
+    search_space_id: int | None = None
+    mentioned_document_ids: list[int] = field(default_factory=list)
+    file_operation_contract: FileOperationContractState | None = None
+    turn_id: str | None = None
+    request_id: str | None = None

surfsense_backend/app/agents/new_chat/feature_flags.py

@@ -103,6 +103,41 @@ class AgentFeatureFlags:
     # Observability — OTel (orthogonal; also requires OTEL_EXPORTER_OTLP_ENDPOINT)
     enable_otel: bool = False
 
+    # Performance — compiled-agent cache (Phase 1 + Phase 2).
+    # When ON, ``create_surfsense_deep_agent`` reuses a previously-compiled
+    # graph if the cache key matches (LLM config + thread + tool surface +
+    # flags + system prompt + filesystem mode). Cuts per-turn agent-build
+    # wall clock from ~4-5s to <50µs on cache hits.
+    #
+    # SAFETY (Phase 2 unblocked this default-on):
+    # All connector mutation tools (``tools/notion``, ``tools/gmail``,
+    # ``tools/google_drive``, ``tools/dropbox``, ``tools/onedrive``,
+    # ``tools/google_calendar``, ``tools/confluence``, ``tools/discord``,
+    # ``tools/teams``, ``tools/luma``, ``connected_accounts``,
+    # ``update_memory``, ``search_surfsense_docs``) now acquire fresh
+    # short-lived ``AsyncSession`` instances per call via
+    # :data:`async_session_maker`. The factory still accepts ``db_session``
+    # for registry compatibility but ``del``'s it immediately — see any
+    # of those files' factory docstrings for the rationale. The ``llm``
+    # closure is per-(provider, model, config_id) which is already in
+    # the cache key, so the LLM is safe to share across cached hits of
+    # the same key. The KB priority middleware reads
+    # ``mentioned_document_ids`` from ``runtime.context`` (Phase 1.5),
+    # not its constructor closure, so the same compiled agent serves
+    # turns with different mention lists correctly.
+    #
+    # Rollback: set ``SURFSENSE_ENABLE_AGENT_CACHE=false`` in the
+    # environment if a regression surfaces. The path is exercised by
+    # the ``tests/unit/agents/new_chat/test_agent_cache_*`` suite.
+    enable_agent_cache: bool = True
+    # Phase 1 (deferred — measure first): pre-build & share the
+    # general-purpose subagent ``CompiledSubAgent`` across cold-cache
+    # misses. Only helps when the outer cache MISSES (cache hits already
+    # reuse the entire SubAgentMiddleware-compiled graph). Off by default
+    # until we have data showing cold misses are frequent enough to
+    # justify the extra global state.
+    enable_agent_cache_share_gp_subagent: bool = False
+
     @classmethod
     def from_env(cls) -> AgentFeatureFlags:
         """Read flags from environment.
@@ -137,6 +172,8 @@ class AgentFeatureFlags:
                 enable_stream_parity_v2=False,
                 enable_plugin_loader=False,
                 enable_otel=False,
+                enable_agent_cache=False,
+                enable_agent_cache_share_gp_subagent=False,
             )
 
         return cls(
@@ -179,6 +216,11 @@ class AgentFeatureFlags:
             enable_plugin_loader=_env_bool("SURFSENSE_ENABLE_PLUGIN_LOADER", False),
             # Observability
             enable_otel=_env_bool("SURFSENSE_ENABLE_OTEL", False),
+            # Performance
+            enable_agent_cache=_env_bool("SURFSENSE_ENABLE_AGENT_CACHE", True),
+            enable_agent_cache_share_gp_subagent=_env_bool(
+                "SURFSENSE_ENABLE_AGENT_CACHE_SHARE_GP_SUBAGENT", False
+            ),
         )
 
     def any_new_middleware_enabled(self) -> bool:

surfsense_backend/app/agents/new_chat/middleware/__init__.py

@@ -24,6 +24,9 @@ from app.agents.new_chat.middleware.file_intent import (
 from app.agents.new_chat.middleware.filesystem import (
     SurfSenseFilesystemMiddleware,
 )
+from app.agents.new_chat.middleware.flatten_system import (
+    FlattenSystemMessageMiddleware,
+)
 from app.agents.new_chat.middleware.kb_persistence import (
     KnowledgeBasePersistenceMiddleware,
     commit_staged_filesystem_state,
@@ -61,6 +64,7 @@ __all__ = [
     "DedupHITLToolCallsMiddleware",
     "DoomLoopMiddleware",
     "FileIntentMiddleware",
+    "FlattenSystemMessageMiddleware",
     "KnowledgeBasePersistenceMiddleware",
     "KnowledgeBaseSearchMiddleware",
     "KnowledgePriorityMiddleware",

surfsense_backend/app/agents/new_chat/middleware/flatten_system.py

@@ -0,0 +1,233 @@
+r"""Coalesce multi-block system messages into a single text block.
+
+Several middlewares in our deepagent stack each call
+``append_to_system_message`` on the way down to the model
+(``TodoListMiddleware``, ``SurfSenseFilesystemMiddleware``,
+``SkillsMiddleware``, ``SubAgentMiddleware`` …). By the time the
+request reaches the LLM, the system message has 5+ separate text blocks.
+
+Anthropic enforces a hard cap of **4 ``cache_control`` blocks per
+request**, and we configure 2 injection points
+(``index: 0`` + ``index: -1``). With ``index: 0`` always targeting
+the prepended ``request.system_message``, this middleware is the
+defensive partner: it guarantees that "the system block" is *one*
+content block, so LiteLLM's ``AnthropicCacheControlHook`` and any
+OpenRouter→Anthropic transformer can never multiply our budget into
+several breakpoints by spreading ``cache_control`` across multiple
+text blocks of a multi-block system content.
+
+Without flattening we used to see::
+
+    OpenrouterException - {"error":{"message":"Provider returned error",
+    "code":400,"metadata":{"raw":"...A maximum of 4 blocks with
+    cache_control may be provided. Found 5."}}}
+
+(Same error class documented in
+https://github.com/BerriAI/litellm/issues/15696 and
+https://github.com/BerriAI/litellm/issues/20485 — the litellm-side fix
+in PR #15395 covers the litellm transformer but does not protect us
+when the OpenRouter SaaS itself does the redistribution.)
+
+A separate fix in :mod:`app.agents.new_chat.prompt_caching` (switching
+the first injection point from ``role: system`` to ``index: 0``)
+neutralises the *primary* cause of the same 400 — multiple
+``SystemMessage``\ s injected by ``before_agent`` middlewares
+(priority/tree/memory/file-intent/anonymous-doc) accumulating across
+turns, each tagged with ``cache_control`` by the ``role: system``
+matcher. This middleware remains useful as defence-in-depth against
+the multi-block redistribution path.
+
+Placement: innermost on the system-message-mutation chain, after every
+appender (``todo``/``filesystem``/``skills``/``subagents``) and after
+summarization, but before ``noop``/``retry``/``fallback`` so each retry
+attempt sees a flattened payload. See ``chat_deepagent.py``.
+
+Idempotent: a string-content system message is left untouched. A list
+that contains anything other than plain text blocks (e.g. an image) is
+also left untouched — those are rare on system messages and we'd lose
+the non-text payload by joining.
+"""
+
+from __future__ import annotations
+
+import logging
+from collections.abc import Awaitable, Callable
+from typing import Any
+
+from langchain.agents.middleware.types import (
+    AgentMiddleware,
+    AgentState,
+    ContextT,
+    ModelRequest,
+    ModelResponse,
+    ResponseT,
+)
+from langchain_core.messages import SystemMessage
+
+logger = logging.getLogger(__name__)
+
+
+def _flatten_text_blocks(content: list[Any]) -> str | None:
+    """Return joined text if every block is a plain ``{"type": "text"}``.
+
+    Returns ``None`` when the list contains anything that isn't a text
+    block we can safely concatenate (image, audio, file, non-standard
+    blocks, dicts with extra non-cache_control fields). The caller
+    leaves the original content untouched in that case rather than
+    silently dropping payload.
+
+    ``cache_control`` on individual blocks is intentionally discarded —
+    the whole point of flattening is to let LiteLLM's
+    ``cache_control_injection_points`` re-place a single breakpoint on
+    the resulting one-block system content.
+    """
+    chunks: list[str] = []
+    for block in content:
+        if isinstance(block, str):
+            chunks.append(block)
+            continue
+        if not isinstance(block, dict):
+            return None
+        if block.get("type") != "text":
+            return None
+        text = block.get("text")
+        if not isinstance(text, str):
+            return None
+        chunks.append(text)
+    return "\n\n".join(chunks)
+
+
+def _flattened_request(
+    request: ModelRequest[ContextT],
+) -> ModelRequest[ContextT] | None:
+    """Return a request with system_message flattened, or ``None`` for no-op."""
+    sys_msg = request.system_message
+    if sys_msg is None:
+        return None
+    content = sys_msg.content
+    if not isinstance(content, list) or len(content) <= 1:
+        return None
+
+    flattened = _flatten_text_blocks(content)
+    if flattened is None:
+        return None
+
+    new_sys = SystemMessage(
+        content=flattened,
+        additional_kwargs=dict(sys_msg.additional_kwargs),
+        response_metadata=dict(sys_msg.response_metadata),
+    )
+    if sys_msg.id is not None:
+        new_sys.id = sys_msg.id
+    return request.override(system_message=new_sys)
+
+
+def _diagnostic_summary(request: ModelRequest[Any]) -> str:
+    """One-line dump of cache_control-relevant request shape.
+
+    Temporary diagnostic to prove where the ``Found N`` cache_control
+    breakpoints are coming from when Anthropic 400s. Removed once the
+    root cause is confirmed and a fix is in place.
+    """
+    sys_msg = request.system_message
+    if sys_msg is None:
+        sys_shape = "none"
+    elif isinstance(sys_msg.content, str):
+        sys_shape = f"str(len={len(sys_msg.content)})"
+    elif isinstance(sys_msg.content, list):
+        sys_shape = f"list(blocks={len(sys_msg.content)})"
+    else:
+        sys_shape = f"other({type(sys_msg.content).__name__})"
+
+    role_hist: list[str] = []
+    multi_block_msgs = 0
+    msgs_with_cc = 0
+    sys_msgs_in_history = 0
+    for m in request.messages:
+        mtype = getattr(m, "type", type(m).__name__)
+        role_hist.append(mtype)
+        if isinstance(m, SystemMessage):
+            sys_msgs_in_history += 1
+        c = getattr(m, "content", None)
+        if isinstance(c, list):
+            multi_block_msgs += 1
+            for blk in c:
+                if isinstance(blk, dict) and "cache_control" in blk:
+                    msgs_with_cc += 1
+                    break
+        if "cache_control" in getattr(m, "additional_kwargs", {}) or {}:
+            msgs_with_cc += 1
+
+    tools = request.tools or []
+    tools_with_cc = 0
+    for t in tools:
+        if isinstance(t, dict) and (
+            "cache_control" in t or "cache_control" in t.get("function", {})
+        ):
+            tools_with_cc += 1
+
+    return (
+        f"sys={sys_shape} msgs={len(request.messages)} "
+        f"sys_msgs_in_history={sys_msgs_in_history} "
+        f"multi_block_msgs={multi_block_msgs} pre_existing_msg_cc={msgs_with_cc} "
+        f"tools={len(tools)} pre_existing_tool_cc={tools_with_cc} "
+        f"roles={role_hist[-8:]}"
+    )
+
+
+class FlattenSystemMessageMiddleware(
+    AgentMiddleware[AgentState[ResponseT], ContextT, ResponseT]
+):
+    """Collapse a multi-text-block system message to a single string.
+
+    Sits innermost on the system-message-mutation chain so it observes
+    every middleware's contribution. Has no other side effect — the
+    body of every block is preserved, just joined with ``"\\n\\n"``.
+    """
+
+    def __init__(self) -> None:
+        super().__init__()
+        self.tools = []
+
+    def wrap_model_call(  # type: ignore[override]
+        self,
+        request: ModelRequest[ContextT],
+        handler: Callable[[ModelRequest[ContextT]], ModelResponse[ResponseT]],
+    ) -> Any:
+        if logger.isEnabledFor(logging.DEBUG):
+            logger.debug("[flatten_system_diag] %s", _diagnostic_summary(request))
+        flattened = _flattened_request(request)
+        if flattened is not None:
+            if logger.isEnabledFor(logging.DEBUG):
+                logger.debug(
+                    "[flatten_system] collapsed %d system blocks to one",
+                    len(request.system_message.content),  # type: ignore[arg-type, union-attr]
+                )
+            return handler(flattened)
+        return handler(request)
+
+    async def awrap_model_call(  # type: ignore[override]
+        self,
+        request: ModelRequest[ContextT],
+        handler: Callable[
+            [ModelRequest[ContextT]], Awaitable[ModelResponse[ResponseT]]
+        ],
+    ) -> Any:
+        if logger.isEnabledFor(logging.DEBUG):
+            logger.debug("[flatten_system_diag] %s", _diagnostic_summary(request))
+        flattened = _flattened_request(request)
+        if flattened is not None:
+            if logger.isEnabledFor(logging.DEBUG):
+                logger.debug(
+                    "[flatten_system] collapsed %d system blocks to one",
+                    len(request.system_message.content),  # type: ignore[arg-type, union-attr]
+                )
+            return await handler(flattened)
+        return await handler(request)
+
+
+__all__ = [
+    "FlattenSystemMessageMiddleware",
+    "_flatten_text_blocks",
+    "_flattened_request",
+]

surfsense_backend/app/agents/new_chat/middleware/knowledge_search.py

@@ -732,7 +732,6 @@ class KnowledgePriorityMiddleware(AgentMiddleware):  # type: ignore[type-arg]
         state: AgentState,
         runtime: Runtime[Any],
     ) -> dict[str, Any] | None:
-        del runtime
         if self.filesystem_mode != FilesystemMode.CLOUD:
             return None
 
@@ -755,7 +754,7 @@ class KnowledgePriorityMiddleware(AgentMiddleware):  # type: ignore[type-arg]
         if anon_doc:
             return self._anon_priority(state, anon_doc)
 
-        return await self._authenticated_priority(state, messages, user_text)
+        return await self._authenticated_priority(state, messages, user_text, runtime)
 
     def _anon_priority(
         self,
@@ -787,6 +786,7 @@ class KnowledgePriorityMiddleware(AgentMiddleware):  # type: ignore[type-arg]
         state: AgentState,
         messages: Sequence[BaseMessage],
         user_text: str,
+        runtime: Runtime[Any] | None = None,
     ) -> dict[str, Any]:
         t0 = asyncio.get_event_loop().time()
         (
@@ -799,13 +799,45 @@ class KnowledgePriorityMiddleware(AgentMiddleware):  # type: ignore[type-arg]
             user_text=user_text,
         )
 
+        # Per-turn ``mentioned_document_ids`` flow:
+        # 1. Preferred path (Phase 1.5+): read from ``runtime.context`` — the
+        #    streaming task supplies a fresh :class:`SurfSenseContextSchema`
+        #    on every ``astream_events`` call, so this list is naturally
+        #    scoped to the current turn. Allows cross-turn graph reuse via
+        #    ``agent_cache``.
+        # 2. Legacy fallback (cache disabled / context not propagated): the
+        #    constructor-injected ``self.mentioned_document_ids`` list. We
+        #    drain it after the first read so a cached graph (no Phase 1.5
+        #    wiring) doesn't keep replaying the same mentions on every
+        #    turn.
+        #
+        # CRITICAL: distinguish "context absent" (legacy caller, no field at
+        # all) from "context provided but empty" (turn with no mentions).
+        # ``ctx_mentions`` is a ``list[int]``; an empty list is falsy in
+        # Python, so a naive ``if ctx_mentions:`` would fall through to the
+        # legacy closure on every no-mention follow-up turn — replaying the
+        # mentions baked in by turn 1's cache-miss build. Always drain the
+        # closure once the runtime path has fired so a cached middleware
+        # instance can never resurrect stale state.
+        mention_ids: list[int] = []
+        ctx = getattr(runtime, "context", None) if runtime is not None else None
+        ctx_mentions = getattr(ctx, "mentioned_document_ids", None) if ctx else None
+        if ctx_mentions is not None:
+            # Runtime path is authoritative — even an empty list means
+            # "this turn has no mentions", NOT "look at the closure".
+            mention_ids = list(ctx_mentions)
+            if self.mentioned_document_ids:
+                self.mentioned_document_ids = []
+        elif self.mentioned_document_ids:
+            mention_ids = list(self.mentioned_document_ids)
+            self.mentioned_document_ids = []
+
         mentioned_results: list[dict[str, Any]] = []
-        if self.mentioned_document_ids:
+        if mention_ids:
             mentioned_results = await fetch_mentioned_documents(
-                document_ids=self.mentioned_document_ids,
+                document_ids=mention_ids,
                 search_space_id=self.search_space_id,
             )
-            self.mentioned_document_ids = []
 
         if is_recency:
             doc_types = _resolve_search_types(

surfsense_backend/app/agents/new_chat/prompt_caching.py

@@ -1,4 +1,4 @@
-"""LiteLLM-native prompt caching configuration for SurfSense agents.
+r"""LiteLLM-native prompt caching configuration for SurfSense agents.
 
 Replaces the legacy ``AnthropicPromptCachingMiddleware`` (which never
 activated for our LiteLLM-based stack — its ``isinstance(model, ChatAnthropic)``
@@ -17,8 +17,20 @@ Coverage:
 
 We inject **two** breakpoints per request:
 
-- ``role: system`` — pins the SurfSense system prompt (provider variant,
-  citation rules, tool catalog, KB tree, skills metadata) into the cache.
+- ``index: 0`` — pins the SurfSense system prompt at the head of the
+  request (provider variant, citation rules, tool catalog, KB tree,
+  skills metadata). The langchain agent factory always prepends
+  ``request.system_message`` at index 0 (see ``factory.py``
+  ``_execute_model_async``), so this targets exactly the main system
+  prompt regardless of how many other ``SystemMessage``\ s the
+  ``before_agent`` injectors (priority, tree, memory, file-intent,
+  anonymous-doc) have inserted into ``state["messages"]``. Using
+  ``role: system`` here would apply ``cache_control`` to **every**
+  system-role message and trip Anthropic's hard cap of 4 cache
+  breakpoints per request once the conversation accumulates enough
+  injected system messages — which surfaces as the upstream 400
+  ``A maximum of 4 blocks with cache_control may be provided. Found N``
+  via OpenRouter→Anthropic.
 - ``index: -1`` — pins the latest message so multi-turn savings compound:
   Anthropic-family providers use longest-matching-prefix lookup, so turn
   N+1 still reads turn N's cache up to the shared prefix.
@@ -51,11 +63,21 @@ if TYPE_CHECKING:
 logger = logging.getLogger(__name__)
 
 
-# Two-breakpoint policy: system + latest message. See module docstring for
-# rationale. Anthropic limits requests to 4 ``cache_control`` blocks; we
-# use 2 here, leaving headroom for Phase-2 tool caching.
+# Two-breakpoint policy: head-of-request + latest message. See module
+# docstring for rationale. Anthropic caps requests at 4 ``cache_control``
+# blocks; we use 2 here, leaving headroom for Phase-2 tool caching.
+#
+# IMPORTANT: ``index: 0`` (not ``role: system``). The deepagent stack's
+# ``before_agent`` middlewares (priority, tree, memory, file-intent,
+# anonymous-doc) insert ``SystemMessage`` instances into
+# ``state["messages"]`` that accumulate across turns. With
+# ``role: system`` the LiteLLM hook would tag *every* one of them with
+# ``cache_control`` and overflow Anthropic's 4-block limit. ``index: 0``
+# always targets the langchain-prepended ``request.system_message``
+# (which our ``FlattenSystemMessageMiddleware`` reduces to a single text
+# block), giving us exactly one stable cache breakpoint.
 _DEFAULT_INJECTION_POINTS: tuple[dict[str, Any], ...] = (
-    {"location": "message", "role": "system"},
+    {"location": "message", "index": 0},
     {"location": "message", "index": -1},
 )
 

surfsense_backend/app/agents/new_chat/tools/confluence/create_page.py

@@ -7,6 +7,7 @@ from sqlalchemy.orm.attributes import flag_modified
 
 from app.agents.new_chat.tools.hitl import request_approval
 from app.connectors.confluence_history import ConfluenceHistoryConnector
+from app.db import async_session_maker
 from app.services.confluence import ConfluenceToolMetadataService
 
 logger = logging.getLogger(__name__)
@@ -18,6 +19,23 @@ def create_create_confluence_page_tool(
     user_id: str | None = None,
     connector_id: int | None = None,
 ):
+    """
+    Factory function to create the create_confluence_page tool.
+
+    The tool acquires its own short-lived ``AsyncSession`` per call via
+    :data:`async_session_maker` so the closure is safe to share across
+    HTTP requests by the compiled-agent cache. Capturing a per-request
+    session here would surface stale/closed sessions on cache hits.
+
+    Args:
+        db_session: Reserved for registry compatibility. Per-call sessions
+            are opened via :data:`async_session_maker` inside the tool body.
+
+    Returns:
+        Configured create_confluence_page tool
+    """
+    del db_session  # per-call session — see docstring
+
     @tool
     async def create_confluence_page(
         title: str,
@@ -42,160 +60,163 @@ def create_create_confluence_page_tool(
         """
         logger.info(f"create_confluence_page called: title='{title}'")
 
-        if db_session is None or search_space_id is None or user_id is None:
+        if search_space_id is None or user_id is None:
             return {
                 "status": "error",
                 "message": "Confluence tool not properly configured.",
             }
 
         try:
-            metadata_service = ConfluenceToolMetadataService(db_session)
-            context = await metadata_service.get_creation_context(
-                search_space_id, user_id
-            )
+            async with async_session_maker() as db_session:
+                metadata_service = ConfluenceToolMetadataService(db_session)
+                context = await metadata_service.get_creation_context(
+                    search_space_id, user_id
+                )
 
-            if "error" in context:
-                return {"status": "error", "message": context["error"]}
+                if "error" in context:
+                    return {"status": "error", "message": context["error"]}
 
-            accounts = context.get("accounts", [])
-            if accounts and all(a.get("auth_expired") for a in accounts):
-                return {
-                    "status": "auth_error",
-                    "message": "All connected Confluence accounts need re-authentication.",
-                    "connector_type": "confluence",
-                }
+                accounts = context.get("accounts", [])
+                if accounts and all(a.get("auth_expired") for a in accounts):
+                    return {
+                        "status": "auth_error",
+                        "message": "All connected Confluence accounts need re-authentication.",
+                        "connector_type": "confluence",
+                    }
 
-            result = request_approval(
-                action_type="confluence_page_creation",
-                tool_name="create_confluence_page",
-                params={
-                    "title": title,
-                    "content": content,
-                    "space_id": space_id,
-                    "connector_id": connector_id,
-                },
-                context=context,
-            )
+                result = request_approval(
+                    action_type="confluence_page_creation",
+                    tool_name="create_confluence_page",
+                    params={
+                        "title": title,
+                        "content": content,
+                        "space_id": space_id,
+                        "connector_id": connector_id,
+                    },
+                    context=context,
+                )
 
-            if result.rejected:
-                return {
-                    "status": "rejected",
-                    "message": "User declined. Do not retry or suggest alternatives.",
-                }
+                if result.rejected:
+                    return {
+                        "status": "rejected",
+                        "message": "User declined. Do not retry or suggest alternatives.",
+                    }
 
-            final_title = result.params.get("title", title)
-            final_content = result.params.get("content", content) or ""
-            final_space_id = result.params.get("space_id", space_id)
-            final_connector_id = result.params.get("connector_id", connector_id)
+                final_title = result.params.get("title", title)
+                final_content = result.params.get("content", content) or ""
+                final_space_id = result.params.get("space_id", space_id)
+                final_connector_id = result.params.get("connector_id", connector_id)
 
-            if not final_title or not final_title.strip():
-                return {"status": "error", "message": "Page title cannot be empty."}
-            if not final_space_id:
-                return {"status": "error", "message": "A space must be selected."}
+                if not final_title or not final_title.strip():
+                    return {"status": "error", "message": "Page title cannot be empty."}
+                if not final_space_id:
+                    return {"status": "error", "message": "A space must be selected."}
 
-            from sqlalchemy.future import select
+                from sqlalchemy.future import select
 
-            from app.db import SearchSourceConnector, SearchSourceConnectorType
+                from app.db import SearchSourceConnector, SearchSourceConnectorType
 
-            actual_connector_id = final_connector_id
-            if actual_connector_id is None:
-                result = await db_session.execute(
-                    select(SearchSourceConnector).filter(
-                        SearchSourceConnector.search_space_id == search_space_id,
-                        SearchSourceConnector.user_id == user_id,
-                        SearchSourceConnector.connector_type
-                        == SearchSourceConnectorType.CONFLUENCE_CONNECTOR,
+                actual_connector_id = final_connector_id
+                if actual_connector_id is None:
+                    result = await db_session.execute(
+                        select(SearchSourceConnector).filter(
+                            SearchSourceConnector.search_space_id == search_space_id,
+                            SearchSourceConnector.user_id == user_id,
+                            SearchSourceConnector.connector_type
+                            == SearchSourceConnectorType.CONFLUENCE_CONNECTOR,
+                        )
                     )
-                )
-                connector = result.scalars().first()
-                if not connector:
-                    return {
-                        "status": "error",
-                        "message": "No Confluence connector found.",
-                    }
-                actual_connector_id = connector.id
-            else:
-                result = await db_session.execute(
-                    select(SearchSourceConnector).filter(
-                        SearchSourceConnector.id == actual_connector_id,
-                        SearchSourceConnector.search_space_id == search_space_id,
-                        SearchSourceConnector.user_id == user_id,
-                        SearchSourceConnector.connector_type
-                        == SearchSourceConnectorType.CONFLUENCE_CONNECTOR,
-                    )
-                )
-                connector = result.scalars().first()
-                if not connector:
-                    return {
-                        "status": "error",
-                        "message": "Selected Confluence connector is invalid.",
-                    }
-
-            try:
-                client = ConfluenceHistoryConnector(
-                    session=db_session, connector_id=actual_connector_id
-                )
-                api_result = await client.create_page(
-                    space_id=final_space_id,
-                    title=final_title,
-                    body=final_content,
-                )
-                await client.close()
-            except Exception as api_err:
-                if (
-                    "http 403" in str(api_err).lower()
-                    or "status code 403" in str(api_err).lower()
-                ):
-                    try:
-                        _conn = connector
-                        _conn.config = {**_conn.config, "auth_expired": True}
-                        flag_modified(_conn, "config")
-                        await db_session.commit()
-                    except Exception:
-                        pass
-                    return {
-                        "status": "insufficient_permissions",
-                        "connector_id": actual_connector_id,
-                        "message": "This Confluence account needs additional permissions. Please re-authenticate in connector settings.",
-                    }
-                raise
-
-            page_id = str(api_result.get("id", ""))
-            page_links = (
-                api_result.get("_links", {}) if isinstance(api_result, dict) else {}
-            )
-            page_url = ""
-            if page_links.get("base") and page_links.get("webui"):
-                page_url = f"{page_links['base']}{page_links['webui']}"
-
-            kb_message_suffix = ""
-            try:
-                from app.services.confluence import ConfluenceKBSyncService
-
-                kb_service = ConfluenceKBSyncService(db_session)
-                kb_result = await kb_service.sync_after_create(
-                    page_id=page_id,
-                    page_title=final_title,
-                    space_id=final_space_id,
-                    body_content=final_content,
-                    connector_id=actual_connector_id,
-                    search_space_id=search_space_id,
-                    user_id=user_id,
-                )
-                if kb_result["status"] == "success":
-                    kb_message_suffix = " Your knowledge base has also been updated."
+                    connector = result.scalars().first()
+                    if not connector:
+                        return {
+                            "status": "error",
+                            "message": "No Confluence connector found.",
+                        }
+                    actual_connector_id = connector.id
                 else:
-                    kb_message_suffix = " This page will be added to your knowledge base in the next scheduled sync."
-            except Exception as kb_err:
-                logger.warning(f"KB sync after create failed: {kb_err}")
-                kb_message_suffix = " This page will be added to your knowledge base in the next scheduled sync."
+                    result = await db_session.execute(
+                        select(SearchSourceConnector).filter(
+                            SearchSourceConnector.id == actual_connector_id,
+                            SearchSourceConnector.search_space_id == search_space_id,
+                            SearchSourceConnector.user_id == user_id,
+                            SearchSourceConnector.connector_type
+                            == SearchSourceConnectorType.CONFLUENCE_CONNECTOR,
+                        )
+                    )
+                    connector = result.scalars().first()
+                    if not connector:
+                        return {
+                            "status": "error",
+                            "message": "Selected Confluence connector is invalid.",
+                        }
 
-            return {
-                "status": "success",
-                "page_id": page_id,
-                "page_url": page_url,
-                "message": f"Confluence page '{final_title}' created successfully.{kb_message_suffix}",
-            }
+                try:
+                    client = ConfluenceHistoryConnector(
+                        session=db_session, connector_id=actual_connector_id
+                    )
+                    api_result = await client.create_page(
+                        space_id=final_space_id,
+                        title=final_title,
+                        body=final_content,
+                    )
+                    await client.close()
+                except Exception as api_err:
+                    if (
+                        "http 403" in str(api_err).lower()
+                        or "status code 403" in str(api_err).lower()
+                    ):
+                        try:
+                            _conn = connector
+                            _conn.config = {**_conn.config, "auth_expired": True}
+                            flag_modified(_conn, "config")
+                            await db_session.commit()
+                        except Exception:
+                            pass
+                        return {
+                            "status": "insufficient_permissions",
+                            "connector_id": actual_connector_id,
+                            "message": "This Confluence account needs additional permissions. Please re-authenticate in connector settings.",
+                        }
+                    raise
+
+                page_id = str(api_result.get("id", ""))
+                page_links = (
+                    api_result.get("_links", {}) if isinstance(api_result, dict) else {}
+                )
+                page_url = ""
+                if page_links.get("base") and page_links.get("webui"):
+                    page_url = f"{page_links['base']}{page_links['webui']}"
+
+                kb_message_suffix = ""
+                try:
+                    from app.services.confluence import ConfluenceKBSyncService
+
+                    kb_service = ConfluenceKBSyncService(db_session)
+                    kb_result = await kb_service.sync_after_create(
+                        page_id=page_id,
+                        page_title=final_title,
+                        space_id=final_space_id,
+                        body_content=final_content,
+                        connector_id=actual_connector_id,
+                        search_space_id=search_space_id,
+                        user_id=user_id,
+                    )
+                    if kb_result["status"] == "success":
+                        kb_message_suffix = (
+                            " Your knowledge base has also been updated."
+                        )
+                    else:
+                        kb_message_suffix = " This page will be added to your knowledge base in the next scheduled sync."
+                except Exception as kb_err:
+                    logger.warning(f"KB sync after create failed: {kb_err}")
+                    kb_message_suffix = " This page will be added to your knowledge base in the next scheduled sync."
+
+                return {
+                    "status": "success",
+                    "page_id": page_id,
+                    "page_url": page_url,
+                    "message": f"Confluence page '{final_title}' created successfully.{kb_message_suffix}",
+                }
 
         except Exception as e:
             from langgraph.errors import GraphInterrupt

surfsense_backend/app/agents/new_chat/tools/confluence/delete_page.py

@@ -7,6 +7,7 @@ from sqlalchemy.orm.attributes import flag_modified
 
 from app.agents.new_chat.tools.hitl import request_approval
 from app.connectors.confluence_history import ConfluenceHistoryConnector
+from app.db import async_session_maker
 from app.services.confluence import ConfluenceToolMetadataService
 
 logger = logging.getLogger(__name__)
@@ -18,6 +19,23 @@ def create_delete_confluence_page_tool(
     user_id: str | None = None,
     connector_id: int | None = None,
 ):
+    """
+    Factory function to create the delete_confluence_page tool.
+
+    The tool acquires its own short-lived ``AsyncSession`` per call via
+    :data:`async_session_maker` so the closure is safe to share across
+    HTTP requests by the compiled-agent cache. Capturing a per-request
+    session here would surface stale/closed sessions on cache hits.
+
+    Args:
+        db_session: Reserved for registry compatibility. Per-call sessions
+            are opened via :data:`async_session_maker` inside the tool body.
+
+    Returns:
+        Configured delete_confluence_page tool
+    """
+    del db_session  # per-call session — see docstring
+
     @tool
     async def delete_confluence_page(
         page_title_or_id: str,
@@ -43,137 +61,143 @@ def create_delete_confluence_page_tool(
             f"delete_confluence_page called: page_title_or_id='{page_title_or_id}'"
         )
 
-        if db_session is None or search_space_id is None or user_id is None:
+        if search_space_id is None or user_id is None:
             return {
                 "status": "error",
                 "message": "Confluence tool not properly configured.",
             }
 
         try:
-            metadata_service = ConfluenceToolMetadataService(db_session)
-            context = await metadata_service.get_deletion_context(
-                search_space_id, user_id, page_title_or_id
-            )
-
-            if "error" in context:
-                error_msg = context["error"]
-                if context.get("auth_expired"):
-                    return {
-                        "status": "auth_error",
-                        "message": error_msg,
-                        "connector_id": context.get("connector_id"),
-                        "connector_type": "confluence",
-                    }
-                if "not found" in error_msg.lower():
-                    return {"status": "not_found", "message": error_msg}
-                return {"status": "error", "message": error_msg}
-
-            page_data = context["page"]
-            page_id = page_data["page_id"]
-            page_title = page_data.get("page_title", "")
-            document_id = page_data["document_id"]
-            connector_id_from_context = context.get("account", {}).get("id")
-
-            result = request_approval(
-                action_type="confluence_page_deletion",
-                tool_name="delete_confluence_page",
-                params={
-                    "page_id": page_id,
-                    "connector_id": connector_id_from_context,
-                    "delete_from_kb": delete_from_kb,
-                },
-                context=context,
-            )
-
-            if result.rejected:
-                return {
-                    "status": "rejected",
-                    "message": "User declined. Do not retry or suggest alternatives.",
-                }
-
-            final_page_id = result.params.get("page_id", page_id)
-            final_connector_id = result.params.get(
-                "connector_id", connector_id_from_context
-            )
-            final_delete_from_kb = result.params.get("delete_from_kb", delete_from_kb)
-
-            from sqlalchemy.future import select
-
-            from app.db import SearchSourceConnector, SearchSourceConnectorType
-
-            if not final_connector_id:
-                return {
-                    "status": "error",
-                    "message": "No connector found for this page.",
-                }
-
-            result = await db_session.execute(
-                select(SearchSourceConnector).filter(
-                    SearchSourceConnector.id == final_connector_id,
-                    SearchSourceConnector.search_space_id == search_space_id,
-                    SearchSourceConnector.user_id == user_id,
-                    SearchSourceConnector.connector_type
-                    == SearchSourceConnectorType.CONFLUENCE_CONNECTOR,
+            async with async_session_maker() as db_session:
+                metadata_service = ConfluenceToolMetadataService(db_session)
+                context = await metadata_service.get_deletion_context(
+                    search_space_id, user_id, page_title_or_id
                 )
-            )
-            connector = result.scalars().first()
-            if not connector:
-                return {
-                    "status": "error",
-                    "message": "Selected Confluence connector is invalid.",
-                }
 
-            try:
-                client = ConfluenceHistoryConnector(
-                    session=db_session, connector_id=final_connector_id
+                if "error" in context:
+                    error_msg = context["error"]
+                    if context.get("auth_expired"):
+                        return {
+                            "status": "auth_error",
+                            "message": error_msg,
+                            "connector_id": context.get("connector_id"),
+                            "connector_type": "confluence",
+                        }
+                    if "not found" in error_msg.lower():
+                        return {"status": "not_found", "message": error_msg}
+                    return {"status": "error", "message": error_msg}
+
+                page_data = context["page"]
+                page_id = page_data["page_id"]
+                page_title = page_data.get("page_title", "")
+                document_id = page_data["document_id"]
+                connector_id_from_context = context.get("account", {}).get("id")
+
+                result = request_approval(
+                    action_type="confluence_page_deletion",
+                    tool_name="delete_confluence_page",
+                    params={
+                        "page_id": page_id,
+                        "connector_id": connector_id_from_context,
+                        "delete_from_kb": delete_from_kb,
+                    },
+                    context=context,
                 )
-                await client.delete_page(final_page_id)
-                await client.close()
-            except Exception as api_err:
-                if (
-                    "http 403" in str(api_err).lower()
-                    or "status code 403" in str(api_err).lower()
-                ):
-                    try:
-                        connector.config = {**connector.config, "auth_expired": True}
-                        flag_modified(connector, "config")
-                        await db_session.commit()
-                    except Exception:
-                        pass
+
+                if result.rejected:
                     return {
-                        "status": "insufficient_permissions",
-                        "connector_id": final_connector_id,
-                        "message": "This Confluence account needs additional permissions. Please re-authenticate in connector settings.",
+                        "status": "rejected",
+                        "message": "User declined. Do not retry or suggest alternatives.",
                     }
-                raise
 
-            deleted_from_kb = False
-            if final_delete_from_kb and document_id:
-                try:
-                    from app.db import Document
+                final_page_id = result.params.get("page_id", page_id)
+                final_connector_id = result.params.get(
+                    "connector_id", connector_id_from_context
+                )
+                final_delete_from_kb = result.params.get(
+                    "delete_from_kb", delete_from_kb
+                )
 
-                    doc_result = await db_session.execute(
-                        select(Document).filter(Document.id == document_id)
+                from sqlalchemy.future import select
+
+                from app.db import SearchSourceConnector, SearchSourceConnectorType
+
+                if not final_connector_id:
+                    return {
+                        "status": "error",
+                        "message": "No connector found for this page.",
+                    }
+
+                result = await db_session.execute(
+                    select(SearchSourceConnector).filter(
+                        SearchSourceConnector.id == final_connector_id,
+                        SearchSourceConnector.search_space_id == search_space_id,
+                        SearchSourceConnector.user_id == user_id,
+                        SearchSourceConnector.connector_type
+                        == SearchSourceConnectorType.CONFLUENCE_CONNECTOR,
                     )
-                    document = doc_result.scalars().first()
-                    if document:
-                        await db_session.delete(document)
-                        await db_session.commit()
-                        deleted_from_kb = True
-                except Exception as e:
-                    logger.error(f"Failed to delete document from KB: {e}")
-                    await db_session.rollback()
+                )
+                connector = result.scalars().first()
+                if not connector:
+                    return {
+                        "status": "error",
+                        "message": "Selected Confluence connector is invalid.",
+                    }
 
-            message = f"Confluence page '{page_title}' deleted successfully."
-            if deleted_from_kb:
-                message += " Also removed from the knowledge base."
+                try:
+                    client = ConfluenceHistoryConnector(
+                        session=db_session, connector_id=final_connector_id
+                    )
+                    await client.delete_page(final_page_id)
+                    await client.close()
+                except Exception as api_err:
+                    if (
+                        "http 403" in str(api_err).lower()
+                        or "status code 403" in str(api_err).lower()
+                    ):
+                        try:
+                            connector.config = {
+                                **connector.config,
+                                "auth_expired": True,
+                            }
+                            flag_modified(connector, "config")
+                            await db_session.commit()
+                        except Exception:
+                            pass
+                        return {
+                            "status": "insufficient_permissions",
+                            "connector_id": final_connector_id,
+                            "message": "This Confluence account needs additional permissions. Please re-authenticate in connector settings.",
+                        }
+                    raise
 
-            return {
-                "status": "success",
-                "page_id": final_page_id,
-                "deleted_from_kb": deleted_from_kb,
-                "message": message,
-            }
+                deleted_from_kb = False
+                if final_delete_from_kb and document_id:
+                    try:
+                        from app.db import Document
+
+                        doc_result = await db_session.execute(
+                            select(Document).filter(Document.id == document_id)
+                        )
+                        document = doc_result.scalars().first()
+                        if document:
+                            await db_session.delete(document)
+                            await db_session.commit()
+                            deleted_from_kb = True
+                    except Exception as e:
+                        logger.error(f"Failed to delete document from KB: {e}")
+                        await db_session.rollback()
+
+                message = f"Confluence page '{page_title}' deleted successfully."
+                if deleted_from_kb:
+                    message += " Also removed from the knowledge base."
+
+                return {
+                    "status": "success",
+                    "page_id": final_page_id,
+                    "deleted_from_kb": deleted_from_kb,
+                    "message": message,
+                }
 
         except Exception as e:
             from langgraph.errors import GraphInterrupt

surfsense_backend/app/agents/new_chat/tools/confluence/update_page.py

@@ -7,6 +7,7 @@ from sqlalchemy.orm.attributes import flag_modified
 
 from app.agents.new_chat.tools.hitl import request_approval
 from app.connectors.confluence_history import ConfluenceHistoryConnector
+from app.db import async_session_maker
 from app.services.confluence import ConfluenceToolMetadataService
 
 logger = logging.getLogger(__name__)
@@ -18,6 +19,23 @@ def create_update_confluence_page_tool(
     user_id: str | None = None,
     connector_id: int | None = None,
 ):
+    """
+    Factory function to create the update_confluence_page tool.
+
+    The tool acquires its own short-lived ``AsyncSession`` per call via
+    :data:`async_session_maker` so the closure is safe to share across
+    HTTP requests by the compiled-agent cache. Capturing a per-request
+    session here would surface stale/closed sessions on cache hits.
+
+    Args:
+        db_session: Reserved for registry compatibility. Per-call sessions
+            are opened via :data:`async_session_maker` inside the tool body.
+
+    Returns:
+        Configured update_confluence_page tool
+    """
+    del db_session  # per-call session — see docstring
+
     @tool
     async def update_confluence_page(
         page_title_or_id: str,
@@ -45,164 +63,168 @@ def create_update_confluence_page_tool(
             f"update_confluence_page called: page_title_or_id='{page_title_or_id}'"
         )
 
-        if db_session is None or search_space_id is None or user_id is None:
+        if search_space_id is None or user_id is None:
             return {
                 "status": "error",
                 "message": "Confluence tool not properly configured.",
             }
 
         try:
-            metadata_service = ConfluenceToolMetadataService(db_session)
-            context = await metadata_service.get_update_context(
-                search_space_id, user_id, page_title_or_id
-            )
+            async with async_session_maker() as db_session:
+                metadata_service = ConfluenceToolMetadataService(db_session)
+                context = await metadata_service.get_update_context(
+                    search_space_id, user_id, page_title_or_id
+                )
 
-            if "error" in context:
-                error_msg = context["error"]
-                if context.get("auth_expired"):
+                if "error" in context:
+                    error_msg = context["error"]
+                    if context.get("auth_expired"):
+                        return {
+                            "status": "auth_error",
+                            "message": error_msg,
+                            "connector_id": context.get("connector_id"),
+                            "connector_type": "confluence",
+                        }
+                    if "not found" in error_msg.lower():
+                        return {"status": "not_found", "message": error_msg}
+                    return {"status": "error", "message": error_msg}
+
+                page_data = context["page"]
+                page_id = page_data["page_id"]
+                current_title = page_data["page_title"]
+                current_body = page_data.get("body", "")
+                current_version = page_data.get("version", 1)
+                document_id = page_data.get("document_id")
+                connector_id_from_context = context.get("account", {}).get("id")
+
+                result = request_approval(
+                    action_type="confluence_page_update",
+                    tool_name="update_confluence_page",
+                    params={
+                        "page_id": page_id,
+                        "document_id": document_id,
+                        "new_title": new_title,
+                        "new_content": new_content,
+                        "version": current_version,
+                        "connector_id": connector_id_from_context,
+                    },
+                    context=context,
+                )
+
+                if result.rejected:
                     return {
-                        "status": "auth_error",
-                        "message": error_msg,
-                        "connector_id": context.get("connector_id"),
-                        "connector_type": "confluence",
+                        "status": "rejected",
+                        "message": "User declined. Do not retry or suggest alternatives.",
                     }
-                if "not found" in error_msg.lower():
-                    return {"status": "not_found", "message": error_msg}
-                return {"status": "error", "message": error_msg}
 
-            page_data = context["page"]
-            page_id = page_data["page_id"]
-            current_title = page_data["page_title"]
-            current_body = page_data.get("body", "")
-            current_version = page_data.get("version", 1)
-            document_id = page_data.get("document_id")
-            connector_id_from_context = context.get("account", {}).get("id")
-
-            result = request_approval(
-                action_type="confluence_page_update",
-                tool_name="update_confluence_page",
-                params={
-                    "page_id": page_id,
-                    "document_id": document_id,
-                    "new_title": new_title,
-                    "new_content": new_content,
-                    "version": current_version,
-                    "connector_id": connector_id_from_context,
-                },
-                context=context,
-            )
-
-            if result.rejected:
-                return {
-                    "status": "rejected",
-                    "message": "User declined. Do not retry or suggest alternatives.",
-                }
-
-            final_page_id = result.params.get("page_id", page_id)
-            final_title = result.params.get("new_title", new_title) or current_title
-            final_content = result.params.get("new_content", new_content)
-            if final_content is None:
-                final_content = current_body
-            final_version = result.params.get("version", current_version)
-            final_connector_id = result.params.get(
-                "connector_id", connector_id_from_context
-            )
-            final_document_id = result.params.get("document_id", document_id)
-
-            from sqlalchemy.future import select
-
-            from app.db import SearchSourceConnector, SearchSourceConnectorType
-
-            if not final_connector_id:
-                return {
-                    "status": "error",
-                    "message": "No connector found for this page.",
-                }
-
-            result = await db_session.execute(
-                select(SearchSourceConnector).filter(
-                    SearchSourceConnector.id == final_connector_id,
-                    SearchSourceConnector.search_space_id == search_space_id,
-                    SearchSourceConnector.user_id == user_id,
-                    SearchSourceConnector.connector_type
-                    == SearchSourceConnectorType.CONFLUENCE_CONNECTOR,
+                final_page_id = result.params.get("page_id", page_id)
+                final_title = result.params.get("new_title", new_title) or current_title
+                final_content = result.params.get("new_content", new_content)
+                if final_content is None:
+                    final_content = current_body
+                final_version = result.params.get("version", current_version)
+                final_connector_id = result.params.get(
+                    "connector_id", connector_id_from_context
                 )
-            )
-            connector = result.scalars().first()
-            if not connector:
-                return {
-                    "status": "error",
-                    "message": "Selected Confluence connector is invalid.",
-                }
+                final_document_id = result.params.get("document_id", document_id)
 
-            try:
-                client = ConfluenceHistoryConnector(
-                    session=db_session, connector_id=final_connector_id
-                )
-                api_result = await client.update_page(
-                    page_id=final_page_id,
-                    title=final_title,
-                    body=final_content,
-                    version_number=final_version + 1,
-                )
-                await client.close()
-            except Exception as api_err:
-                if (
-                    "http 403" in str(api_err).lower()
-                    or "status code 403" in str(api_err).lower()
-                ):
-                    try:
-                        connector.config = {**connector.config, "auth_expired": True}
-                        flag_modified(connector, "config")
-                        await db_session.commit()
-                    except Exception:
-                        pass
+                from sqlalchemy.future import select
+
+                from app.db import SearchSourceConnector, SearchSourceConnectorType
+
+                if not final_connector_id:
                     return {
-                        "status": "insufficient_permissions",
-                        "connector_id": final_connector_id,
-                        "message": "This Confluence account needs additional permissions. Please re-authenticate in connector settings.",
+                        "status": "error",
+                        "message": "No connector found for this page.",
                     }
-                raise
 
-            page_links = (
-                api_result.get("_links", {}) if isinstance(api_result, dict) else {}
-            )
-            page_url = ""
-            if page_links.get("base") and page_links.get("webui"):
-                page_url = f"{page_links['base']}{page_links['webui']}"
-
-            kb_message_suffix = ""
-            if final_document_id:
-                try:
-                    from app.services.confluence import ConfluenceKBSyncService
-
-                    kb_service = ConfluenceKBSyncService(db_session)
-                    kb_result = await kb_service.sync_after_update(
-                        document_id=final_document_id,
-                        page_id=final_page_id,
-                        user_id=user_id,
-                        search_space_id=search_space_id,
+                result = await db_session.execute(
+                    select(SearchSourceConnector).filter(
+                        SearchSourceConnector.id == final_connector_id,
+                        SearchSourceConnector.search_space_id == search_space_id,
+                        SearchSourceConnector.user_id == user_id,
+                        SearchSourceConnector.connector_type
+                        == SearchSourceConnectorType.CONFLUENCE_CONNECTOR,
                     )
-                    if kb_result["status"] == "success":
-                        kb_message_suffix = (
-                            " Your knowledge base has also been updated."
+                )
+                connector = result.scalars().first()
+                if not connector:
+                    return {
+                        "status": "error",
+                        "message": "Selected Confluence connector is invalid.",
+                    }
+
+                try:
+                    client = ConfluenceHistoryConnector(
+                        session=db_session, connector_id=final_connector_id
+                    )
+                    api_result = await client.update_page(
+                        page_id=final_page_id,
+                        title=final_title,
+                        body=final_content,
+                        version_number=final_version + 1,
+                    )
+                    await client.close()
+                except Exception as api_err:
+                    if (
+                        "http 403" in str(api_err).lower()
+                        or "status code 403" in str(api_err).lower()
+                    ):
+                        try:
+                            connector.config = {
+                                **connector.config,
+                                "auth_expired": True,
+                            }
+                            flag_modified(connector, "config")
+                            await db_session.commit()
+                        except Exception:
+                            pass
+                        return {
+                            "status": "insufficient_permissions",
+                            "connector_id": final_connector_id,
+                            "message": "This Confluence account needs additional permissions. Please re-authenticate in connector settings.",
+                        }
+                    raise
+
+                page_links = (
+                    api_result.get("_links", {}) if isinstance(api_result, dict) else {}
+                )
+                page_url = ""
+                if page_links.get("base") and page_links.get("webui"):
+                    page_url = f"{page_links['base']}{page_links['webui']}"
+
+                kb_message_suffix = ""
+                if final_document_id:
+                    try:
+                        from app.services.confluence import ConfluenceKBSyncService
+
+                        kb_service = ConfluenceKBSyncService(db_session)
+                        kb_result = await kb_service.sync_after_update(
+                            document_id=final_document_id,
+                            page_id=final_page_id,
+                            user_id=user_id,
+                            search_space_id=search_space_id,
                         )
-                    else:
+                        if kb_result["status"] == "success":
+                            kb_message_suffix = (
+                                " Your knowledge base has also been updated."
+                            )
+                        else:
+                            kb_message_suffix = (
+                                " The knowledge base will be updated in the next sync."
+                            )
+                    except Exception as kb_err:
+                        logger.warning(f"KB sync after update failed: {kb_err}")
                         kb_message_suffix = (
                             " The knowledge base will be updated in the next sync."
                         )
-                except Exception as kb_err:
-                    logger.warning(f"KB sync after update failed: {kb_err}")
-                    kb_message_suffix = (
-                        " The knowledge base will be updated in the next sync."
-                    )
 
-            return {
-                "status": "success",
-                "page_id": final_page_id,
-                "page_url": page_url,
-                "message": f"Confluence page '{final_title}' updated successfully.{kb_message_suffix}",
-            }
+                return {
+                    "status": "success",
+                    "page_id": final_page_id,
+                    "page_url": page_url,
+                    "message": f"Confluence page '{final_title}' updated successfully.{kb_message_suffix}",
+                }
 
         except Exception as e:
             from langgraph.errors import GraphInterrupt

surfsense_backend/app/agents/new_chat/tools/connected_accounts.py

@@ -17,7 +17,7 @@ from pydantic import BaseModel, Field
 from sqlalchemy.ext.asyncio import AsyncSession
 from sqlalchemy.future import select
 
-from app.db import SearchSourceConnector, SearchSourceConnectorType
+from app.db import SearchSourceConnector, SearchSourceConnectorType, async_session_maker
 from app.services.mcp_oauth.registry import MCP_SERVICES
 
 logger = logging.getLogger(__name__)
@@ -53,6 +53,23 @@ def create_get_connected_accounts_tool(
     search_space_id: int,
     user_id: str,
 ) -> StructuredTool:
+    """Factory function to create the get_connected_accounts tool.
+
+    The tool acquires its own short-lived ``AsyncSession`` per call via
+    :data:`async_session_maker` so the closure is safe to share across
+    HTTP requests by the compiled-agent cache. Capturing a per-request
+    session here would surface stale/closed sessions on cache hits.
+
+    Args:
+        db_session: Reserved for registry compatibility. Per-call sessions
+            are opened via :data:`async_session_maker` inside the tool body.
+        search_space_id: Search space ID to scope account discovery to.
+        user_id: User ID to scope account discovery to.
+
+    Returns:
+        Configured StructuredTool for connected-accounts discovery.
+    """
+    del db_session  # per-call session — see docstring
 
     async def _run(service: str) -> list[dict[str, Any]]:
         svc_cfg = MCP_SERVICES.get(service)
@@ -68,40 +85,41 @@ def create_get_connected_accounts_tool(
         except ValueError:
             return [{"error": f"Connector type '{svc_cfg.connector_type}' not found."}]
 
-        result = await db_session.execute(
-            select(SearchSourceConnector).filter(
-                SearchSourceConnector.search_space_id == search_space_id,
-                SearchSourceConnector.user_id == user_id,
-                SearchSourceConnector.connector_type == connector_type,
+        async with async_session_maker() as db_session:
+            result = await db_session.execute(
+                select(SearchSourceConnector).filter(
+                    SearchSourceConnector.search_space_id == search_space_id,
+                    SearchSourceConnector.user_id == user_id,
+                    SearchSourceConnector.connector_type == connector_type,
+                )
             )
-        )
-        connectors = result.scalars().all()
+            connectors = result.scalars().all()
 
-        if not connectors:
-            return [
-                {
-                    "error": f"No {svc_cfg.name} accounts connected. Ask the user to connect one in settings."
+            if not connectors:
+                return [
+                    {
+                        "error": f"No {svc_cfg.name} accounts connected. Ask the user to connect one in settings."
+                    }
+                ]
+
+            is_multi = len(connectors) > 1
+
+            accounts: list[dict[str, Any]] = []
+            for conn in connectors:
+                cfg = conn.config or {}
+                entry: dict[str, Any] = {
+                    "connector_id": conn.id,
+                    "display_name": _extract_display_name(conn),
+                    "service": service,
                 }
-            ]
+                if is_multi:
+                    entry["tool_prefix"] = f"{service}_{conn.id}"
+                for key in svc_cfg.account_metadata_keys:
+                    if key in cfg:
+                        entry[key] = cfg[key]
+                accounts.append(entry)
 
-        is_multi = len(connectors) > 1
-
-        accounts: list[dict[str, Any]] = []
-        for conn in connectors:
-            cfg = conn.config or {}
-            entry: dict[str, Any] = {
-                "connector_id": conn.id,
-                "display_name": _extract_display_name(conn),
-                "service": service,
-            }
-            if is_multi:
-                entry["tool_prefix"] = f"{service}_{conn.id}"
-            for key in svc_cfg.account_metadata_keys:
-                if key in cfg:
-                    entry[key] = cfg[key]
-            accounts.append(entry)
-
-        return accounts
+            return accounts
 
     return StructuredTool(
         name="get_connected_accounts",

surfsense_backend/app/agents/new_chat/tools/discord/list_channels.py

@@ -5,6 +5,8 @@ import httpx
 from langchain_core.tools import tool
 from sqlalchemy.ext.asyncio import AsyncSession
 
+from app.db import async_session_maker
+
 from ._auth import DISCORD_API, get_bot_token, get_discord_connector, get_guild_id
 
 logger = logging.getLogger(__name__)
@@ -15,6 +17,23 @@ def create_list_discord_channels_tool(
     search_space_id: int | None = None,
     user_id: str | None = None,
 ):
+    """
+    Factory function to create the list_discord_channels tool.
+
+    The tool acquires its own short-lived ``AsyncSession`` per call via
+    :data:`async_session_maker` so the closure is safe to share across
+    HTTP requests by the compiled-agent cache. Capturing a per-request
+    session here would surface stale/closed sessions on cache hits.
+
+    Args:
+        db_session: Reserved for registry compatibility. Per-call sessions
+            are opened via :data:`async_session_maker` inside the tool body.
+
+    Returns:
+        Configured list_discord_channels tool
+    """
+    del db_session  # per-call session — see docstring
+
     @tool
     async def list_discord_channels() -> dict[str, Any]:
         """List text channels in the connected Discord server.
@@ -22,59 +41,60 @@ def create_list_discord_channels_tool(
         Returns:
             Dictionary with status and a list of channels (id, name).
         """
-        if db_session is None or search_space_id is None or user_id is None:
+        if search_space_id is None or user_id is None:
             return {
                 "status": "error",
                 "message": "Discord tool not properly configured.",
             }
 
         try:
-            connector = await get_discord_connector(
-                db_session, search_space_id, user_id
-            )
-            if not connector:
-                return {"status": "error", "message": "No Discord connector found."}
-
-            guild_id = get_guild_id(connector)
-            if not guild_id:
-                return {
-                    "status": "error",
-                    "message": "No guild ID in Discord connector config.",
-                }
-
-            token = get_bot_token(connector)
-
-            async with httpx.AsyncClient() as client:
-                resp = await client.get(
-                    f"{DISCORD_API}/guilds/{guild_id}/channels",
-                    headers={"Authorization": f"Bot {token}"},
-                    timeout=15.0,
+            async with async_session_maker() as db_session:
+                connector = await get_discord_connector(
+                    db_session, search_space_id, user_id
                 )
+                if not connector:
+                    return {"status": "error", "message": "No Discord connector found."}
 
-            if resp.status_code == 401:
-                return {
-                    "status": "auth_error",
-                    "message": "Discord bot token is invalid.",
-                    "connector_type": "discord",
-                }
-            if resp.status_code != 200:
-                return {
-                    "status": "error",
-                    "message": f"Discord API error: {resp.status_code}",
-                }
+                guild_id = get_guild_id(connector)
+                if not guild_id:
+                    return {
+                        "status": "error",
+                        "message": "No guild ID in Discord connector config.",
+                    }
 
-            # Type 0 = text channel
-            channels = [
-                {"id": ch["id"], "name": ch["name"]}
-                for ch in resp.json()
-                if ch.get("type") == 0
-            ]
-            return {
-                "status": "success",
-                "guild_id": guild_id,
-                "channels": channels,
-                "total": len(channels),
-            }
+                token = get_bot_token(connector)
+
+                async with httpx.AsyncClient() as client:
+                    resp = await client.get(
+                        f"{DISCORD_API}/guilds/{guild_id}/channels",
+                        headers={"Authorization": f"Bot {token}"},
+                        timeout=15.0,
+                    )
+
+                if resp.status_code == 401:
+                    return {
+                        "status": "auth_error",
+                        "message": "Discord bot token is invalid.",
+                        "connector_type": "discord",
+                    }
+                if resp.status_code != 200:
+                    return {
+                        "status": "error",
+                        "message": f"Discord API error: {resp.status_code}",
+                    }
+
+                # Type 0 = text channel
+                channels = [
+                    {"id": ch["id"], "name": ch["name"]}
+                    for ch in resp.json()
+                    if ch.get("type") == 0
+                ]
+                return {
+                    "status": "success",
+                    "guild_id": guild_id,
+                    "channels": channels,
+                    "total": len(channels),
+                }
 
         except Exception as e:
             from langgraph.errors import GraphInterrupt

surfsense_backend/app/agents/new_chat/tools/discord/read_messages.py

@@ -5,6 +5,8 @@ import httpx
 from langchain_core.tools import tool
 from sqlalchemy.ext.asyncio import AsyncSession
 
+from app.db import async_session_maker
+
 from ._auth import DISCORD_API, get_bot_token, get_discord_connector
 
 logger = logging.getLogger(__name__)
@@ -15,6 +17,23 @@ def create_read_discord_messages_tool(
     search_space_id: int | None = None,
     user_id: str | None = None,
 ):
+    """
+    Factory function to create the read_discord_messages tool.
+
+    The tool acquires its own short-lived ``AsyncSession`` per call via
+    :data:`async_session_maker` so the closure is safe to share across
+    HTTP requests by the compiled-agent cache. Capturing a per-request
+    session here would surface stale/closed sessions on cache hits.
+
+    Args:
+        db_session: Reserved for registry compatibility. Per-call sessions
+            are opened via :data:`async_session_maker` inside the tool body.
+
+    Returns:
+        Configured read_discord_messages tool
+    """
+    del db_session  # per-call session — see docstring
+
     @tool
     async def read_discord_messages(
         channel_id: str,
@@ -30,7 +49,7 @@ def create_read_discord_messages_tool(
             Dictionary with status and a list of messages including
             id, author, content, timestamp.
         """
-        if db_session is None or search_space_id is None or user_id is None:
+        if search_space_id is None or user_id is None:
             return {
                 "status": "error",
                 "message": "Discord tool not properly configured.",
@@ -39,55 +58,56 @@ def create_read_discord_messages_tool(
         limit = min(limit, 50)
 
         try:
-            connector = await get_discord_connector(
-                db_session, search_space_id, user_id
-            )
-            if not connector:
-                return {"status": "error", "message": "No Discord connector found."}
-
-            token = get_bot_token(connector)
-
-            async with httpx.AsyncClient() as client:
-                resp = await client.get(
-                    f"{DISCORD_API}/channels/{channel_id}/messages",
-                    headers={"Authorization": f"Bot {token}"},
-                    params={"limit": limit},
-                    timeout=15.0,
+            async with async_session_maker() as db_session:
+                connector = await get_discord_connector(
+                    db_session, search_space_id, user_id
                 )
+                if not connector:
+                    return {"status": "error", "message": "No Discord connector found."}
 
-            if resp.status_code == 401:
-                return {
-                    "status": "auth_error",
-                    "message": "Discord bot token is invalid.",
-                    "connector_type": "discord",
-                }
-            if resp.status_code == 403:
-                return {
-                    "status": "error",
-                    "message": "Bot lacks permission to read this channel.",
-                }
-            if resp.status_code != 200:
-                return {
-                    "status": "error",
-                    "message": f"Discord API error: {resp.status_code}",
-                }
+                token = get_bot_token(connector)
 
-            messages = [
-                {
-                    "id": m["id"],
-                    "author": m.get("author", {}).get("username", "Unknown"),
-                    "content": m.get("content", ""),
-                    "timestamp": m.get("timestamp", ""),
-                }
-                for m in resp.json()
-            ]
+                async with httpx.AsyncClient() as client:
+                    resp = await client.get(
+                        f"{DISCORD_API}/channels/{channel_id}/messages",
+                        headers={"Authorization": f"Bot {token}"},
+                        params={"limit": limit},
+                        timeout=15.0,
+                    )
 
-            return {
-                "status": "success",
-                "channel_id": channel_id,
-                "messages": messages,
-                "total": len(messages),
-            }
+                if resp.status_code == 401:
+                    return {
+                        "status": "auth_error",
+                        "message": "Discord bot token is invalid.",
+                        "connector_type": "discord",
+                    }
+                if resp.status_code == 403:
+                    return {
+                        "status": "error",
+                        "message": "Bot lacks permission to read this channel.",
+                    }
+                if resp.status_code != 200:
+                    return {
+                        "status": "error",
+                        "message": f"Discord API error: {resp.status_code}",
+                    }
+
+                messages = [
+                    {
+                        "id": m["id"],
+                        "author": m.get("author", {}).get("username", "Unknown"),
+                        "content": m.get("content", ""),
+                        "timestamp": m.get("timestamp", ""),
+                    }
+                    for m in resp.json()
+                ]
+
+                return {
+                    "status": "success",
+                    "channel_id": channel_id,
+                    "messages": messages,
+                    "total": len(messages),
+                }
 
         except Exception as e:
             from langgraph.errors import GraphInterrupt

surfsense_backend/app/agents/new_chat/tools/discord/send_message.py

@@ -6,6 +6,7 @@ from langchain_core.tools import tool
 from sqlalchemy.ext.asyncio import AsyncSession
 
 from app.agents.new_chat.tools.hitl import request_approval
+from app.db import async_session_maker
 
 from ._auth import DISCORD_API, get_bot_token, get_discord_connector
 
@@ -17,6 +18,23 @@ def create_send_discord_message_tool(
     search_space_id: int | None = None,
     user_id: str | None = None,
 ):
+    """
+    Factory function to create the send_discord_message tool.
+
+    The tool acquires its own short-lived ``AsyncSession`` per call via
+    :data:`async_session_maker` so the closure is safe to share across
+    HTTP requests by the compiled-agent cache. Capturing a per-request
+    session here would surface stale/closed sessions on cache hits.
+
+    Args:
+        db_session: Reserved for registry compatibility. Per-call sessions
+            are opened via :data:`async_session_maker` inside the tool body.
+
+    Returns:
+        Configured send_discord_message tool
+    """
+    del db_session  # per-call session — see docstring
+
     @tool
     async def send_discord_message(
         channel_id: str,
@@ -34,7 +52,7 @@ def create_send_discord_message_tool(
             IMPORTANT:
             - If status is "rejected", the user explicitly declined. Do NOT retry.
         """
-        if db_session is None or search_space_id is None or user_id is None:
+        if search_space_id is None or user_id is None:
             return {
                 "status": "error",
                 "message": "Discord tool not properly configured.",
@@ -47,64 +65,65 @@ def create_send_discord_message_tool(
             }
 
         try:
-            connector = await get_discord_connector(
-                db_session, search_space_id, user_id
-            )
-            if not connector:
-                return {"status": "error", "message": "No Discord connector found."}
+            async with async_session_maker() as db_session:
+                connector = await get_discord_connector(
+                    db_session, search_space_id, user_id
+                )
+                if not connector:
+                    return {"status": "error", "message": "No Discord connector found."}
 
-            result = request_approval(
-                action_type="discord_send_message",
-                tool_name="send_discord_message",
-                params={"channel_id": channel_id, "content": content},
-                context={"connector_id": connector.id},
-            )
-
-            if result.rejected:
-                return {
-                    "status": "rejected",
-                    "message": "User declined. Message was not sent.",
-                }
-
-            final_content = result.params.get("content", content)
-            final_channel = result.params.get("channel_id", channel_id)
-
-            token = get_bot_token(connector)
-
-            async with httpx.AsyncClient() as client:
-                resp = await client.post(
-                    f"{DISCORD_API}/channels/{final_channel}/messages",
-                    headers={
-                        "Authorization": f"Bot {token}",
-                        "Content-Type": "application/json",
-                    },
-                    json={"content": final_content},
-                    timeout=15.0,
+                result = request_approval(
+                    action_type="discord_send_message",
+                    tool_name="send_discord_message",
+                    params={"channel_id": channel_id, "content": content},
+                    context={"connector_id": connector.id},
                 )
 
-            if resp.status_code == 401:
-                return {
-                    "status": "auth_error",
-                    "message": "Discord bot token is invalid.",
-                    "connector_type": "discord",
-                }
-            if resp.status_code == 403:
-                return {
-                    "status": "error",
-                    "message": "Bot lacks permission to send messages in this channel.",
-                }
-            if resp.status_code not in (200, 201):
-                return {
-                    "status": "error",
-                    "message": f"Discord API error: {resp.status_code}",
-                }
+                if result.rejected:
+                    return {
+                        "status": "rejected",
+                        "message": "User declined. Message was not sent.",
+                    }
 
-            msg_data = resp.json()
-            return {
-                "status": "success",
-                "message_id": msg_data.get("id"),
-                "message": f"Message sent to channel {final_channel}.",
-            }
+                final_content = result.params.get("content", content)
+                final_channel = result.params.get("channel_id", channel_id)
+
+                token = get_bot_token(connector)
+
+                async with httpx.AsyncClient() as client:
+                    resp = await client.post(
+                        f"{DISCORD_API}/channels/{final_channel}/messages",
+                        headers={
+                            "Authorization": f"Bot {token}",
+                            "Content-Type": "application/json",
+                        },
+                        json={"content": final_content},
+                        timeout=15.0,
+                    )
+
+                if resp.status_code == 401:
+                    return {
+                        "status": "auth_error",
+                        "message": "Discord bot token is invalid.",
+                        "connector_type": "discord",
+                    }
+                if resp.status_code == 403:
+                    return {
+                        "status": "error",
+                        "message": "Bot lacks permission to send messages in this channel.",
+                    }
+                if resp.status_code not in (200, 201):
+                    return {
+                        "status": "error",
+                        "message": f"Discord API error: {resp.status_code}",
+                    }
+
+                msg_data = resp.json()
+                return {
+                    "status": "success",
+                    "message_id": msg_data.get("id"),
+                    "message": f"Message sent to channel {final_channel}.",
+                }
 
         except Exception as e:
             from langgraph.errors import GraphInterrupt

surfsense_backend/app/agents/new_chat/tools/dropbox/create_file.py

@@ -10,7 +10,7 @@ from sqlalchemy.future import select
 
 from app.agents.new_chat.tools.hitl import request_approval
 from app.connectors.dropbox.client import DropboxClient
-from app.db import SearchSourceConnector, SearchSourceConnectorType
+from app.db import SearchSourceConnector, SearchSourceConnectorType, async_session_maker
 
 logger = logging.getLogger(__name__)
 
@@ -59,6 +59,23 @@ def create_create_dropbox_file_tool(
     search_space_id: int | None = None,
     user_id: str | None = None,
 ):
+    """
+    Factory function to create the create_dropbox_file tool.
+
+    The tool acquires its own short-lived ``AsyncSession`` per call via
+    :data:`async_session_maker` so the closure is safe to share across
+    HTTP requests by the compiled-agent cache. Capturing a per-request
+    session here would surface stale/closed sessions on cache hits.
+
+    Args:
+        db_session: Reserved for registry compatibility. Per-call sessions
+            are opened via :data:`async_session_maker` inside the tool body.
+
+    Returns:
+        Configured create_dropbox_file tool
+    """
+    del db_session  # per-call session — see docstring
+
     @tool
     async def create_dropbox_file(
         name: str,
@@ -82,184 +99,191 @@ def create_create_dropbox_file_tool(
             f"create_dropbox_file called: name='{name}', file_type='{file_type}'"
         )
 
-        if db_session is None or search_space_id is None or user_id is None:
+        if search_space_id is None or user_id is None:
             return {
                 "status": "error",
                 "message": "Dropbox tool not properly configured.",
             }
 
         try:
-            result = await db_session.execute(
-                select(SearchSourceConnector).filter(
-                    SearchSourceConnector.search_space_id == search_space_id,
-                    SearchSourceConnector.user_id == user_id,
-                    SearchSourceConnector.connector_type
-                    == SearchSourceConnectorType.DROPBOX_CONNECTOR,
-                )
-            )
-            connectors = result.scalars().all()
-
-            if not connectors:
-                return {
-                    "status": "error",
-                    "message": "No Dropbox connector found. Please connect Dropbox in your workspace settings.",
-                }
-
-            accounts = []
-            for c in connectors:
-                cfg = c.config or {}
-                accounts.append(
-                    {
-                        "id": c.id,
-                        "name": c.name,
-                        "user_email": cfg.get("user_email"),
-                        "auth_expired": cfg.get("auth_expired", False),
-                    }
-                )
-
-            if all(a.get("auth_expired") for a in accounts):
-                return {
-                    "status": "auth_error",
-                    "message": "All connected Dropbox accounts need re-authentication.",
-                    "connector_type": "dropbox",
-                }
-
-            parent_folders: dict[int, list[dict[str, str]]] = {}
-            for acc in accounts:
-                cid = acc["id"]
-                if acc.get("auth_expired"):
-                    parent_folders[cid] = []
-                    continue
-                try:
-                    client = DropboxClient(session=db_session, connector_id=cid)
-                    items, err = await client.list_folder("")
-                    if err:
-                        logger.warning(
-                            "Failed to list folders for connector %s: %s", cid, err
-                        )
-                        parent_folders[cid] = []
-                    else:
-                        parent_folders[cid] = [
-                            {
-                                "folder_path": item.get("path_lower", ""),
-                                "name": item["name"],
-                            }
-                            for item in items
-                            if item.get(".tag") == "folder" and item.get("name")
-                        ]
-                except Exception:
-                    logger.warning(
-                        "Error fetching folders for connector %s", cid, exc_info=True
-                    )
-                    parent_folders[cid] = []
-
-            context: dict[str, Any] = {
-                "accounts": accounts,
-                "parent_folders": parent_folders,
-                "supported_types": _SUPPORTED_TYPES,
-            }
-
-            result = request_approval(
-                action_type="dropbox_file_creation",
-                tool_name="create_dropbox_file",
-                params={
-                    "name": name,
-                    "file_type": file_type,
-                    "content": content,
-                    "connector_id": None,
-                    "parent_folder_path": None,
-                },
-                context=context,
-            )
-
-            if result.rejected:
-                return {
-                    "status": "rejected",
-                    "message": "User declined. Do not retry or suggest alternatives.",
-                }
-
-            final_name = result.params.get("name", name)
-            final_file_type = result.params.get("file_type", file_type)
-            final_content = result.params.get("content", content)
-            final_connector_id = result.params.get("connector_id")
-            final_parent_folder_path = result.params.get("parent_folder_path")
-
-            if not final_name or not final_name.strip():
-                return {"status": "error", "message": "File name cannot be empty."}
-
-            final_name = _ensure_extension(final_name, final_file_type)
-
-            if final_connector_id is not None:
+            async with async_session_maker() as db_session:
                 result = await db_session.execute(
                     select(SearchSourceConnector).filter(
-                        SearchSourceConnector.id == final_connector_id,
                         SearchSourceConnector.search_space_id == search_space_id,
                         SearchSourceConnector.user_id == user_id,
                         SearchSourceConnector.connector_type
                         == SearchSourceConnectorType.DROPBOX_CONNECTOR,
                     )
                 )
-                connector = result.scalars().first()
-            else:
-                connector = connectors[0]
+                connectors = result.scalars().all()
 
-            if not connector:
-                return {
-                    "status": "error",
-                    "message": "Selected Dropbox connector is invalid.",
+                if not connectors:
+                    return {
+                        "status": "error",
+                        "message": "No Dropbox connector found. Please connect Dropbox in your workspace settings.",
+                    }
+
+                accounts = []
+                for c in connectors:
+                    cfg = c.config or {}
+                    accounts.append(
+                        {
+                            "id": c.id,
+                            "name": c.name,
+                            "user_email": cfg.get("user_email"),
+                            "auth_expired": cfg.get("auth_expired", False),
+                        }
+                    )
+
+                if all(a.get("auth_expired") for a in accounts):
+                    return {
+                        "status": "auth_error",
+                        "message": "All connected Dropbox accounts need re-authentication.",
+                        "connector_type": "dropbox",
+                    }
+
+                parent_folders: dict[int, list[dict[str, str]]] = {}
+                for acc in accounts:
+                    cid = acc["id"]
+                    if acc.get("auth_expired"):
+                        parent_folders[cid] = []
+                        continue
+                    try:
+                        client = DropboxClient(session=db_session, connector_id=cid)
+                        items, err = await client.list_folder("")
+                        if err:
+                            logger.warning(
+                                "Failed to list folders for connector %s: %s", cid, err
+                            )
+                            parent_folders[cid] = []
+                        else:
+                            parent_folders[cid] = [
+                                {
+                                    "folder_path": item.get("path_lower", ""),
+                                    "name": item["name"],
+                                }
+                                for item in items
+                                if item.get(".tag") == "folder" and item.get("name")
+                            ]
+                    except Exception:
+                        logger.warning(
+                            "Error fetching folders for connector %s",
+                            cid,
+                            exc_info=True,
+                        )
+                        parent_folders[cid] = []
+
+                context: dict[str, Any] = {
+                    "accounts": accounts,
+                    "parent_folders": parent_folders,
+                    "supported_types": _SUPPORTED_TYPES,
                 }
 
-            client = DropboxClient(session=db_session, connector_id=connector.id)
-
-            parent_path = final_parent_folder_path or ""
-            file_path = (
-                f"{parent_path}/{final_name}" if parent_path else f"/{final_name}"
-            )
-
-            if final_file_type == "paper":
-                created = await client.create_paper_doc(file_path, final_content or "")
-                file_id = created.get("file_id", "")
-                web_url = created.get("url", "")
-            else:
-                docx_bytes = _markdown_to_docx(final_content or "")
-                created = await client.upload_file(
-                    file_path, docx_bytes, mode="add", autorename=True
+                result = request_approval(
+                    action_type="dropbox_file_creation",
+                    tool_name="create_dropbox_file",
+                    params={
+                        "name": name,
+                        "file_type": file_type,
+                        "content": content,
+                        "connector_id": None,
+                        "parent_folder_path": None,
+                    },
+                    context=context,
                 )
-                file_id = created.get("id", "")
-                web_url = ""
 
-            logger.info(f"Dropbox file created: id={file_id}, name={final_name}")
+                if result.rejected:
+                    return {
+                        "status": "rejected",
+                        "message": "User declined. Do not retry or suggest alternatives.",
+                    }
 
-            kb_message_suffix = ""
-            try:
-                from app.services.dropbox import DropboxKBSyncService
+                final_name = result.params.get("name", name)
+                final_file_type = result.params.get("file_type", file_type)
+                final_content = result.params.get("content", content)
+                final_connector_id = result.params.get("connector_id")
+                final_parent_folder_path = result.params.get("parent_folder_path")
 
-                kb_service = DropboxKBSyncService(db_session)
-                kb_result = await kb_service.sync_after_create(
-                    file_id=file_id,
-                    file_name=final_name,
-                    file_path=file_path,
-                    web_url=web_url,
-                    content=final_content,
-                    connector_id=connector.id,
-                    search_space_id=search_space_id,
-                    user_id=user_id,
-                )
-                if kb_result["status"] == "success":
-                    kb_message_suffix = " Your knowledge base has also been updated."
+                if not final_name or not final_name.strip():
+                    return {"status": "error", "message": "File name cannot be empty."}
+
+                final_name = _ensure_extension(final_name, final_file_type)
+
+                if final_connector_id is not None:
+                    result = await db_session.execute(
+                        select(SearchSourceConnector).filter(
+                            SearchSourceConnector.id == final_connector_id,
+                            SearchSourceConnector.search_space_id == search_space_id,
+                            SearchSourceConnector.user_id == user_id,
+                            SearchSourceConnector.connector_type
+                            == SearchSourceConnectorType.DROPBOX_CONNECTOR,
+                        )
+                    )
+                    connector = result.scalars().first()
                 else:
-                    kb_message_suffix = " This file will be added to your knowledge base in the next scheduled sync."
-            except Exception as kb_err:
-                logger.warning(f"KB sync after create failed: {kb_err}")
-                kb_message_suffix = " This file will be added to your knowledge base in the next scheduled sync."
+                    connector = connectors[0]
 
-            return {
-                "status": "success",
-                "file_id": file_id,
-                "name": final_name,
-                "web_url": web_url,
-                "message": f"Successfully created '{final_name}' in Dropbox.{kb_message_suffix}",
-            }
+                if not connector:
+                    return {
+                        "status": "error",
+                        "message": "Selected Dropbox connector is invalid.",
+                    }
+
+                client = DropboxClient(session=db_session, connector_id=connector.id)
+
+                parent_path = final_parent_folder_path or ""
+                file_path = (
+                    f"{parent_path}/{final_name}" if parent_path else f"/{final_name}"
+                )
+
+                if final_file_type == "paper":
+                    created = await client.create_paper_doc(
+                        file_path, final_content or ""
+                    )
+                    file_id = created.get("file_id", "")
+                    web_url = created.get("url", "")
+                else:
+                    docx_bytes = _markdown_to_docx(final_content or "")
+                    created = await client.upload_file(
+                        file_path, docx_bytes, mode="add", autorename=True
+                    )
+                    file_id = created.get("id", "")
+                    web_url = ""
+
+                logger.info(f"Dropbox file created: id={file_id}, name={final_name}")
+
+                kb_message_suffix = ""
+                try:
+                    from app.services.dropbox import DropboxKBSyncService
+
+                    kb_service = DropboxKBSyncService(db_session)
+                    kb_result = await kb_service.sync_after_create(
+                        file_id=file_id,
+                        file_name=final_name,
+                        file_path=file_path,
+                        web_url=web_url,
+                        content=final_content,
+                        connector_id=connector.id,
+                        search_space_id=search_space_id,
+                        user_id=user_id,
+                    )
+                    if kb_result["status"] == "success":
+                        kb_message_suffix = (
+                            " Your knowledge base has also been updated."
+                        )
+                    else:
+                        kb_message_suffix = " This file will be added to your knowledge base in the next scheduled sync."
+                except Exception as kb_err:
+                    logger.warning(f"KB sync after create failed: {kb_err}")
+                    kb_message_suffix = " This file will be added to your knowledge base in the next scheduled sync."
+
+                return {
+                    "status": "success",
+                    "file_id": file_id,
+                    "name": final_name,
+                    "web_url": web_url,
+                    "message": f"Successfully created '{final_name}' in Dropbox.{kb_message_suffix}",
+                }
 
         except Exception as e:
             from langgraph.errors import GraphInterrupt

surfsense_backend/app/agents/new_chat/tools/dropbox/trash_file.py

@@ -13,6 +13,7 @@ from app.db import (
     DocumentType,
     SearchSourceConnector,
     SearchSourceConnectorType,
+    async_session_maker,
 )
 
 logger = logging.getLogger(__name__)
@@ -23,6 +24,23 @@ def create_delete_dropbox_file_tool(
     search_space_id: int | None = None,
     user_id: str | None = None,
 ):
+    """
+    Factory function to create the delete_dropbox_file tool.
+
+    The tool acquires its own short-lived ``AsyncSession`` per call via
+    :data:`async_session_maker` so the closure is safe to share across
+    HTTP requests by the compiled-agent cache. Capturing a per-request
+    session here would surface stale/closed sessions on cache hits.
+
+    Args:
+        db_session: Reserved for registry compatibility. Per-call sessions
+            are opened via :data:`async_session_maker` inside the tool body.
+
+    Returns:
+        Configured delete_dropbox_file tool
+    """
+    del db_session  # per-call session — see docstring
+
     @tool
     async def delete_dropbox_file(
         file_name: str,
@@ -55,33 +73,14 @@ def create_delete_dropbox_file_tool(
             f"delete_dropbox_file called: file_name='{file_name}', delete_from_kb={delete_from_kb}"
         )
 
-        if db_session is None or search_space_id is None or user_id is None:
+        if search_space_id is None or user_id is None:
             return {
                 "status": "error",
                 "message": "Dropbox tool not properly configured.",
             }
 
         try:
-            doc_result = await db_session.execute(
-                select(Document)
-                .join(
-                    SearchSourceConnector,
-                    Document.connector_id == SearchSourceConnector.id,
-                )
-                .filter(
-                    and_(
-                        Document.search_space_id == search_space_id,
-                        Document.document_type == DocumentType.DROPBOX_FILE,
-                        func.lower(Document.title) == func.lower(file_name),
-                        SearchSourceConnector.user_id == user_id,
-                    )
-                )
-                .order_by(Document.updated_at.desc().nullslast())
-                .limit(1)
-            )
-            document = doc_result.scalars().first()
-
-            if not document:
+            async with async_session_maker() as db_session:
                 doc_result = await db_session.execute(
                     select(Document)
                     .join(
@@ -92,13 +91,7 @@ def create_delete_dropbox_file_tool(
                         and_(
                             Document.search_space_id == search_space_id,
                             Document.document_type == DocumentType.DROPBOX_FILE,
-                            func.lower(
-                                cast(
-                                    Document.document_metadata["dropbox_file_name"],
-                                    String,
-                                )
-                            )
-                            == func.lower(file_name),
+                            func.lower(Document.title) == func.lower(file_name),
                             SearchSourceConnector.user_id == user_id,
                         )
                     )
@@ -107,99 +100,63 @@ def create_delete_dropbox_file_tool(
                 )
                 document = doc_result.scalars().first()
 
-            if not document:
-                return {
-                    "status": "not_found",
-                    "message": (
-                        f"File '{file_name}' not found in your indexed Dropbox files. "
-                        "This could mean: (1) the file doesn't exist, (2) it hasn't been indexed yet, "
-                        "or (3) the file name is different."
-                    ),
-                }
-
-            if not document.connector_id:
-                return {
-                    "status": "error",
-                    "message": "Document has no associated connector.",
-                }
-
-            meta = document.document_metadata or {}
-            file_path = meta.get("dropbox_path")
-            file_id = meta.get("dropbox_file_id")
-            document_id = document.id
-
-            if not file_path:
-                return {
-                    "status": "error",
-                    "message": "File path is missing. Please re-index the file.",
-                }
-
-            conn_result = await db_session.execute(
-                select(SearchSourceConnector).filter(
-                    and_(
-                        SearchSourceConnector.id == document.connector_id,
-                        SearchSourceConnector.search_space_id == search_space_id,
-                        SearchSourceConnector.user_id == user_id,
-                        SearchSourceConnector.connector_type
-                        == SearchSourceConnectorType.DROPBOX_CONNECTOR,
+                if not document:
+                    doc_result = await db_session.execute(
+                        select(Document)
+                        .join(
+                            SearchSourceConnector,
+                            Document.connector_id == SearchSourceConnector.id,
+                        )
+                        .filter(
+                            and_(
+                                Document.search_space_id == search_space_id,
+                                Document.document_type == DocumentType.DROPBOX_FILE,
+                                func.lower(
+                                    cast(
+                                        Document.document_metadata["dropbox_file_name"],
+                                        String,
+                                    )
+                                )
+                                == func.lower(file_name),
+                                SearchSourceConnector.user_id == user_id,
+                            )
+                        )
+                        .order_by(Document.updated_at.desc().nullslast())
+                        .limit(1)
                     )
-                )
-            )
-            connector = conn_result.scalars().first()
-            if not connector:
-                return {
-                    "status": "error",
-                    "message": "Dropbox connector not found or access denied.",
-                }
+                    document = doc_result.scalars().first()
 
-            cfg = connector.config or {}
-            if cfg.get("auth_expired"):
-                return {
-                    "status": "auth_error",
-                    "message": "Dropbox account needs re-authentication. Please re-authenticate in your connector settings.",
-                    "connector_type": "dropbox",
-                }
+                if not document:
+                    return {
+                        "status": "not_found",
+                        "message": (
+                            f"File '{file_name}' not found in your indexed Dropbox files. "
+                            "This could mean: (1) the file doesn't exist, (2) it hasn't been indexed yet, "
+                            "or (3) the file name is different."
+                        ),
+                    }
 
-            context = {
-                "file": {
-                    "file_id": file_id,
-                    "file_path": file_path,
-                    "name": file_name,
-                    "document_id": document_id,
-                },
-                "account": {
-                    "id": connector.id,
-                    "name": connector.name,
-                    "user_email": cfg.get("user_email"),
-                },
-            }
+                if not document.connector_id:
+                    return {
+                        "status": "error",
+                        "message": "Document has no associated connector.",
+                    }
 
-            result = request_approval(
-                action_type="dropbox_file_trash",
-                tool_name="delete_dropbox_file",
-                params={
-                    "file_path": file_path,
-                    "connector_id": connector.id,
-                    "delete_from_kb": delete_from_kb,
-                },
-                context=context,
-            )
+                meta = document.document_metadata or {}
+                file_path = meta.get("dropbox_path")
+                file_id = meta.get("dropbox_file_id")
+                document_id = document.id
 
-            if result.rejected:
-                return {
-                    "status": "rejected",
-                    "message": "User declined. Do not retry or suggest alternatives.",
-                }
+                if not file_path:
+                    return {
+                        "status": "error",
+                        "message": "File path is missing. Please re-index the file.",
+                    }
 
-            final_file_path = result.params.get("file_path", file_path)
-            final_connector_id = result.params.get("connector_id", connector.id)
-            final_delete_from_kb = result.params.get("delete_from_kb", delete_from_kb)
-
-            if final_connector_id != connector.id:
-                result = await db_session.execute(
+                conn_result = await db_session.execute(
                     select(SearchSourceConnector).filter(
                         and_(
-                            SearchSourceConnector.id == final_connector_id,
+                            SearchSourceConnector.id == document.connector_id,
                             SearchSourceConnector.search_space_id == search_space_id,
                             SearchSourceConnector.user_id == user_id,
                             SearchSourceConnector.connector_type
@@ -207,61 +164,128 @@ def create_delete_dropbox_file_tool(
                         )
                     )
                 )
-                validated_connector = result.scalars().first()
-                if not validated_connector:
+                connector = conn_result.scalars().first()
+                if not connector:
                     return {
                         "status": "error",
-                        "message": "Selected Dropbox connector is invalid or has been disconnected.",
+                        "message": "Dropbox connector not found or access denied.",
                     }
-                actual_connector_id = validated_connector.id
-            else:
-                actual_connector_id = connector.id
 
-            logger.info(
-                f"Deleting Dropbox file: path='{final_file_path}', connector={actual_connector_id}"
-            )
+                cfg = connector.config or {}
+                if cfg.get("auth_expired"):
+                    return {
+                        "status": "auth_error",
+                        "message": "Dropbox account needs re-authentication. Please re-authenticate in your connector settings.",
+                        "connector_type": "dropbox",
+                    }
 
-            client = DropboxClient(session=db_session, connector_id=actual_connector_id)
-            await client.delete_file(final_file_path)
+                context = {
+                    "file": {
+                        "file_id": file_id,
+                        "file_path": file_path,
+                        "name": file_name,
+                        "document_id": document_id,
+                    },
+                    "account": {
+                        "id": connector.id,
+                        "name": connector.name,
+                        "user_email": cfg.get("user_email"),
+                    },
+                }
 
-            logger.info(f"Dropbox file deleted: path={final_file_path}")
-
-            trash_result: dict[str, Any] = {
-                "status": "success",
-                "file_id": file_id,
-                "message": f"Successfully deleted '{file_name}' from Dropbox.",
-            }
-
-            deleted_from_kb = False
-            if final_delete_from_kb and document_id:
-                try:
-                    doc_result = await db_session.execute(
-                        select(Document).filter(Document.id == document_id)
-                    )
-                    doc = doc_result.scalars().first()
-                    if doc:
-                        await db_session.delete(doc)
-                        await db_session.commit()
-                        deleted_from_kb = True
-                        logger.info(
-                            f"Deleted document {document_id} from knowledge base"
-                        )
-                    else:
-                        logger.warning(f"Document {document_id} not found in KB")
-                except Exception as e:
-                    logger.error(f"Failed to delete document from KB: {e}")
-                    await db_session.rollback()
-                    trash_result["warning"] = (
-                        f"File deleted, but failed to remove from knowledge base: {e!s}"
-                    )
-
-            trash_result["deleted_from_kb"] = deleted_from_kb
-            if deleted_from_kb:
-                trash_result["message"] = (
-                    f"{trash_result.get('message', '')} (also removed from knowledge base)"
+                result = request_approval(
+                    action_type="dropbox_file_trash",
+                    tool_name="delete_dropbox_file",
+                    params={
+                        "file_path": file_path,
+                        "connector_id": connector.id,
+                        "delete_from_kb": delete_from_kb,
+                    },
+                    context=context,
                 )
 
-            return trash_result
+                if result.rejected:
+                    return {
+                        "status": "rejected",
+                        "message": "User declined. Do not retry or suggest alternatives.",
+                    }
+
+                final_file_path = result.params.get("file_path", file_path)
+                final_connector_id = result.params.get("connector_id", connector.id)
+                final_delete_from_kb = result.params.get(
+                    "delete_from_kb", delete_from_kb
+                )
+
+                if final_connector_id != connector.id:
+                    result = await db_session.execute(
+                        select(SearchSourceConnector).filter(
+                            and_(
+                                SearchSourceConnector.id == final_connector_id,
+                                SearchSourceConnector.search_space_id
+                                == search_space_id,
+                                SearchSourceConnector.user_id == user_id,
+                                SearchSourceConnector.connector_type
+                                == SearchSourceConnectorType.DROPBOX_CONNECTOR,
+                            )
+                        )
+                    )
+                    validated_connector = result.scalars().first()
+                    if not validated_connector:
+                        return {
+                            "status": "error",
+                            "message": "Selected Dropbox connector is invalid or has been disconnected.",
+                        }
+                    actual_connector_id = validated_connector.id
+                else:
+                    actual_connector_id = connector.id
+
+                logger.info(
+                    f"Deleting Dropbox file: path='{final_file_path}', connector={actual_connector_id}"
+                )
+
+                client = DropboxClient(
+                    session=db_session, connector_id=actual_connector_id
+                )
+                await client.delete_file(final_file_path)
+
+                logger.info(f"Dropbox file deleted: path={final_file_path}")
+
+                trash_result: dict[str, Any] = {
+                    "status": "success",
+                    "file_id": file_id,
+                    "message": f"Successfully deleted '{file_name}' from Dropbox.",
+                }
+
+                deleted_from_kb = False
+                if final_delete_from_kb and document_id:
+                    try:
+                        doc_result = await db_session.execute(
+                            select(Document).filter(Document.id == document_id)
+                        )
+                        doc = doc_result.scalars().first()
+                        if doc:
+                            await db_session.delete(doc)
+                            await db_session.commit()
+                            deleted_from_kb = True
+                            logger.info(
+                                f"Deleted document {document_id} from knowledge base"
+                            )
+                        else:
+                            logger.warning(f"Document {document_id} not found in KB")
+                    except Exception as e:
+                        logger.error(f"Failed to delete document from KB: {e}")
+                        await db_session.rollback()
+                        trash_result["warning"] = (
+                            f"File deleted, but failed to remove from knowledge base: {e!s}"
+                        )
+
+                trash_result["deleted_from_kb"] = deleted_from_kb
+                if deleted_from_kb:
+                    trash_result["message"] = (
+                        f"{trash_result.get('message', '')} (also removed from knowledge base)"
+                    )
+
+                return trash_result
 
         except Exception as e:
             from langgraph.errors import GraphInterrupt

surfsense_backend/app/agents/new_chat/tools/gmail/create_draft.py

@@ -9,6 +9,7 @@ from langchain_core.tools import tool
 from sqlalchemy.ext.asyncio import AsyncSession
 
 from app.agents.new_chat.tools.hitl import request_approval
+from app.db import async_session_maker
 from app.services.gmail import GmailToolMetadataService
 
 logger = logging.getLogger(__name__)
@@ -19,6 +20,23 @@ def create_create_gmail_draft_tool(
     search_space_id: int | None = None,
     user_id: str | None = None,
 ):
+    """
+    Factory function to create the create_gmail_draft tool.
+
+    The tool acquires its own short-lived ``AsyncSession`` per call via
+    :data:`async_session_maker` so the closure is safe to share across
+    HTTP requests by the compiled-agent cache. Capturing a per-request
+    session here would surface stale/closed sessions on cache hits.
+
+    Args:
+        db_session: Reserved for registry compatibility. Per-call sessions
+            are opened via :data:`async_session_maker` inside the tool body.
+
+    Returns:
+        Configured create_gmail_draft tool
+    """
+    del db_session  # per-call session — see docstring
+
     @tool
     async def create_gmail_draft(
         to: str,
@@ -57,267 +75,276 @@ def create_create_gmail_draft_tool(
         """
         logger.info(f"create_gmail_draft called: to='{to}', subject='{subject}'")
 
-        if db_session is None or search_space_id is None or user_id is None:
+        if search_space_id is None or user_id is None:
             return {
                 "status": "error",
                 "message": "Gmail tool not properly configured. Please contact support.",
             }
 
         try:
-            metadata_service = GmailToolMetadataService(db_session)
-            context = await metadata_service.get_creation_context(
-                search_space_id, user_id
-            )
+            async with async_session_maker() as db_session:
+                metadata_service = GmailToolMetadataService(db_session)
+                context = await metadata_service.get_creation_context(
+                    search_space_id, user_id
+                )
 
-            if "error" in context:
-                logger.error(f"Failed to fetch creation context: {context['error']}")
-                return {"status": "error", "message": context["error"]}
-
-            accounts = context.get("accounts", [])
-            if accounts and all(a.get("auth_expired") for a in accounts):
-                logger.warning("All Gmail accounts have expired authentication")
-                return {
-                    "status": "auth_error",
-                    "message": "All connected Gmail accounts need re-authentication. Please re-authenticate in your connector settings.",
-                    "connector_type": "gmail",
-                }
-
-            logger.info(
-                f"Requesting approval for creating Gmail draft: to='{to}', subject='{subject}'"
-            )
-            result = request_approval(
-                action_type="gmail_draft_creation",
-                tool_name="create_gmail_draft",
-                params={
-                    "to": to,
-                    "subject": subject,
-                    "body": body,
-                    "cc": cc,
-                    "bcc": bcc,
-                    "connector_id": None,
-                },
-                context=context,
-            )
-
-            if result.rejected:
-                return {
-                    "status": "rejected",
-                    "message": "User declined. The draft was not created. Do not ask again or suggest alternatives.",
-                }
-
-            final_to = result.params.get("to", to)
-            final_subject = result.params.get("subject", subject)
-            final_body = result.params.get("body", body)
-            final_cc = result.params.get("cc", cc)
-            final_bcc = result.params.get("bcc", bcc)
-            final_connector_id = result.params.get("connector_id")
-
-            from sqlalchemy.future import select
-
-            from app.db import SearchSourceConnector, SearchSourceConnectorType
-
-            _gmail_types = [
-                SearchSourceConnectorType.GOOGLE_GMAIL_CONNECTOR,
-                SearchSourceConnectorType.COMPOSIO_GMAIL_CONNECTOR,
-            ]
-
-            if final_connector_id is not None:
-                result = await db_session.execute(
-                    select(SearchSourceConnector).filter(
-                        SearchSourceConnector.id == final_connector_id,
-                        SearchSourceConnector.search_space_id == search_space_id,
-                        SearchSourceConnector.user_id == user_id,
-                        SearchSourceConnector.connector_type.in_(_gmail_types),
+                if "error" in context:
+                    logger.error(
+                        f"Failed to fetch creation context: {context['error']}"
                     )
-                )
-                connector = result.scalars().first()
-                if not connector:
+                    return {"status": "error", "message": context["error"]}
+
+                accounts = context.get("accounts", [])
+                if accounts and all(a.get("auth_expired") for a in accounts):
+                    logger.warning("All Gmail accounts have expired authentication")
                     return {
-                        "status": "error",
-                        "message": "Selected Gmail connector is invalid or has been disconnected.",
+                        "status": "auth_error",
+                        "message": "All connected Gmail accounts need re-authentication. Please re-authenticate in your connector settings.",
+                        "connector_type": "gmail",
                     }
-                actual_connector_id = connector.id
-            else:
-                result = await db_session.execute(
-                    select(SearchSourceConnector).filter(
-                        SearchSourceConnector.search_space_id == search_space_id,
-                        SearchSourceConnector.user_id == user_id,
-                        SearchSourceConnector.connector_type.in_(_gmail_types),
+
+                logger.info(
+                    f"Requesting approval for creating Gmail draft: to='{to}', subject='{subject}'"
+                )
+                result = request_approval(
+                    action_type="gmail_draft_creation",
+                    tool_name="create_gmail_draft",
+                    params={
+                        "to": to,
+                        "subject": subject,
+                        "body": body,
+                        "cc": cc,
+                        "bcc": bcc,
+                        "connector_id": None,
+                    },
+                    context=context,
+                )
+
+                if result.rejected:
+                    return {
+                        "status": "rejected",
+                        "message": "User declined. The draft was not created. Do not ask again or suggest alternatives.",
+                    }
+
+                final_to = result.params.get("to", to)
+                final_subject = result.params.get("subject", subject)
+                final_body = result.params.get("body", body)
+                final_cc = result.params.get("cc", cc)
+                final_bcc = result.params.get("bcc", bcc)
+                final_connector_id = result.params.get("connector_id")
+
+                from sqlalchemy.future import select
+
+                from app.db import SearchSourceConnector, SearchSourceConnectorType
+
+                _gmail_types = [
+                    SearchSourceConnectorType.GOOGLE_GMAIL_CONNECTOR,
+                    SearchSourceConnectorType.COMPOSIO_GMAIL_CONNECTOR,
+                ]
+
+                if final_connector_id is not None:
+                    result = await db_session.execute(
+                        select(SearchSourceConnector).filter(
+                            SearchSourceConnector.id == final_connector_id,
+                            SearchSourceConnector.search_space_id == search_space_id,
+                            SearchSourceConnector.user_id == user_id,
+                            SearchSourceConnector.connector_type.in_(_gmail_types),
+                        )
                     )
-                )
-                connector = result.scalars().first()
-                if not connector:
-                    return {
-                        "status": "error",
-                        "message": "No Gmail connector found. Please connect Gmail in your workspace settings.",
-                    }
-                actual_connector_id = connector.id
-
-            logger.info(
-                f"Creating Gmail draft: to='{final_to}', subject='{final_subject}', connector={actual_connector_id}"
-            )
-
-            is_composio_gmail = (
-                connector.connector_type
-                == SearchSourceConnectorType.COMPOSIO_GMAIL_CONNECTOR
-            )
-            if is_composio_gmail:
-                cca_id = connector.config.get("composio_connected_account_id")
-                if not cca_id:
-                    return {
-                        "status": "error",
-                        "message": "Composio connected account ID not found for this Gmail connector.",
-                    }
-            else:
-                from google.oauth2.credentials import Credentials
-
-                from app.config import config
-                from app.utils.oauth_security import TokenEncryption
-
-                config_data = dict(connector.config)
-                token_encrypted = config_data.get("_token_encrypted", False)
-                if token_encrypted and config.SECRET_KEY:
-                    token_encryption = TokenEncryption(config.SECRET_KEY)
-                    if config_data.get("token"):
-                        config_data["token"] = token_encryption.decrypt_token(
-                            config_data["token"]
-                        )
-                    if config_data.get("refresh_token"):
-                        config_data["refresh_token"] = token_encryption.decrypt_token(
-                            config_data["refresh_token"]
-                        )
-                    if config_data.get("client_secret"):
-                        config_data["client_secret"] = token_encryption.decrypt_token(
-                            config_data["client_secret"]
+                    connector = result.scalars().first()
+                    if not connector:
+                        return {
+                            "status": "error",
+                            "message": "Selected Gmail connector is invalid or has been disconnected.",
+                        }
+                    actual_connector_id = connector.id
+                else:
+                    result = await db_session.execute(
+                        select(SearchSourceConnector).filter(
+                            SearchSourceConnector.search_space_id == search_space_id,
+                            SearchSourceConnector.user_id == user_id,
+                            SearchSourceConnector.connector_type.in_(_gmail_types),
                         )
+                    )
+                    connector = result.scalars().first()
+                    if not connector:
+                        return {
+                            "status": "error",
+                            "message": "No Gmail connector found. Please connect Gmail in your workspace settings.",
+                        }
+                    actual_connector_id = connector.id
 
-                exp = config_data.get("expiry", "")
-                if exp:
-                    exp = exp.replace("Z", "")
-
-                creds = Credentials(
-                    token=config_data.get("token"),
-                    refresh_token=config_data.get("refresh_token"),
-                    token_uri=config_data.get("token_uri"),
-                    client_id=config_data.get("client_id"),
-                    client_secret=config_data.get("client_secret"),
-                    scopes=config_data.get("scopes", []),
-                    expiry=datetime.fromisoformat(exp) if exp else None,
+                logger.info(
+                    f"Creating Gmail draft: to='{final_to}', subject='{final_subject}', connector={actual_connector_id}"
                 )
 
-            message = MIMEText(final_body)
-            message["to"] = final_to
-            message["subject"] = final_subject
-            if final_cc:
-                message["cc"] = final_cc
-            if final_bcc:
-                message["bcc"] = final_bcc
-            raw = base64.urlsafe_b64encode(message.as_bytes()).decode()
-
-            try:
+                is_composio_gmail = (
+                    connector.connector_type
+                    == SearchSourceConnectorType.COMPOSIO_GMAIL_CONNECTOR
+                )
                 if is_composio_gmail:
-                    from app.agents.new_chat.tools.gmail.composio_helpers import (
-                        execute_composio_gmail_tool,
-                        split_recipients,
-                    )
-
-                    created, error = await execute_composio_gmail_tool(
-                        connector,
-                        user_id,
-                        "GMAIL_CREATE_EMAIL_DRAFT",
-                        {
-                            "user_id": "me",
-                            "recipient_email": final_to,
-                            "subject": final_subject,
-                            "body": final_body,
-                            "cc": split_recipients(final_cc),
-                            "bcc": split_recipients(final_bcc),
-                            "is_html": False,
-                        },
-                    )
-                    if error:
-                        raise RuntimeError(error)
-                    if not isinstance(created, dict):
-                        created = {}
+                    cca_id = connector.config.get("composio_connected_account_id")
+                    if not cca_id:
+                        return {
+                            "status": "error",
+                            "message": "Composio connected account ID not found for this Gmail connector.",
+                        }
                 else:
-                    from googleapiclient.discovery import build
+                    from google.oauth2.credentials import Credentials
 
-                    gmail_service = build("gmail", "v1", credentials=creds)
-                    created = await asyncio.get_event_loop().run_in_executor(
-                        None,
-                        lambda: (
-                            gmail_service.users()
-                            .drafts()
-                            .create(userId="me", body={"message": {"raw": raw}})
-                            .execute()
-                        ),
-                    )
-            except Exception as api_err:
-                from googleapiclient.errors import HttpError
+                    from app.config import config
+                    from app.utils.oauth_security import TokenEncryption
 
-                if isinstance(api_err, HttpError) and api_err.resp.status == 403:
-                    logger.warning(
-                        f"Insufficient permissions for connector {actual_connector_id}: {api_err}"
-                    )
-                    try:
-                        from sqlalchemy.orm.attributes import flag_modified
-
-                        _res = await db_session.execute(
-                            select(SearchSourceConnector).where(
-                                SearchSourceConnector.id == actual_connector_id
+                    config_data = dict(connector.config)
+                    token_encrypted = config_data.get("_token_encrypted", False)
+                    if token_encrypted and config.SECRET_KEY:
+                        token_encryption = TokenEncryption(config.SECRET_KEY)
+                        if config_data.get("token"):
+                            config_data["token"] = token_encryption.decrypt_token(
+                                config_data["token"]
                             )
+                        if config_data.get("refresh_token"):
+                            config_data["refresh_token"] = (
+                                token_encryption.decrypt_token(
+                                    config_data["refresh_token"]
+                                )
+                            )
+                        if config_data.get("client_secret"):
+                            config_data["client_secret"] = (
+                                token_encryption.decrypt_token(
+                                    config_data["client_secret"]
+                                )
+                            )
+
+                    exp = config_data.get("expiry", "")
+                    if exp:
+                        exp = exp.replace("Z", "")
+
+                    creds = Credentials(
+                        token=config_data.get("token"),
+                        refresh_token=config_data.get("refresh_token"),
+                        token_uri=config_data.get("token_uri"),
+                        client_id=config_data.get("client_id"),
+                        client_secret=config_data.get("client_secret"),
+                        scopes=config_data.get("scopes", []),
+                        expiry=datetime.fromisoformat(exp) if exp else None,
+                    )
+
+                message = MIMEText(final_body)
+                message["to"] = final_to
+                message["subject"] = final_subject
+                if final_cc:
+                    message["cc"] = final_cc
+                if final_bcc:
+                    message["bcc"] = final_bcc
+                raw = base64.urlsafe_b64encode(message.as_bytes()).decode()
+
+                try:
+                    if is_composio_gmail:
+                        from app.agents.new_chat.tools.gmail.composio_helpers import (
+                            execute_composio_gmail_tool,
+                            split_recipients,
                         )
-                        _conn = _res.scalar_one_or_none()
-                        if _conn and not _conn.config.get("auth_expired"):
-                            _conn.config = {**_conn.config, "auth_expired": True}
-                            flag_modified(_conn, "config")
-                            await db_session.commit()
-                    except Exception:
+
+                        created, error = await execute_composio_gmail_tool(
+                            connector,
+                            user_id,
+                            "GMAIL_CREATE_EMAIL_DRAFT",
+                            {
+                                "user_id": "me",
+                                "recipient_email": final_to,
+                                "subject": final_subject,
+                                "body": final_body,
+                                "cc": split_recipients(final_cc),
+                                "bcc": split_recipients(final_bcc),
+                                "is_html": False,
+                            },
+                        )
+                        if error:
+                            raise RuntimeError(error)
+                        if not isinstance(created, dict):
+                            created = {}
+                    else:
+                        from googleapiclient.discovery import build
+
+                        gmail_service = build("gmail", "v1", credentials=creds)
+                        created = await asyncio.get_event_loop().run_in_executor(
+                            None,
+                            lambda: (
+                                gmail_service.users()
+                                .drafts()
+                                .create(userId="me", body={"message": {"raw": raw}})
+                                .execute()
+                            ),
+                        )
+                except Exception as api_err:
+                    from googleapiclient.errors import HttpError
+
+                    if isinstance(api_err, HttpError) and api_err.resp.status == 403:
                         logger.warning(
-                            "Failed to persist auth_expired for connector %s",
-                            actual_connector_id,
-                            exc_info=True,
+                            f"Insufficient permissions for connector {actual_connector_id}: {api_err}"
                         )
-                    return {
-                        "status": "insufficient_permissions",
-                        "connector_id": actual_connector_id,
-                        "message": "This Gmail account needs additional permissions. Please re-authenticate in connector settings.",
-                    }
-                raise
+                        try:
+                            from sqlalchemy.orm.attributes import flag_modified
 
-            logger.info(f"Gmail draft created: id={created.get('id')}")
+                            _res = await db_session.execute(
+                                select(SearchSourceConnector).where(
+                                    SearchSourceConnector.id == actual_connector_id
+                                )
+                            )
+                            _conn = _res.scalar_one_or_none()
+                            if _conn and not _conn.config.get("auth_expired"):
+                                _conn.config = {**_conn.config, "auth_expired": True}
+                                flag_modified(_conn, "config")
+                                await db_session.commit()
+                        except Exception:
+                            logger.warning(
+                                "Failed to persist auth_expired for connector %s",
+                                actual_connector_id,
+                                exc_info=True,
+                            )
+                        return {
+                            "status": "insufficient_permissions",
+                            "connector_id": actual_connector_id,
+                            "message": "This Gmail account needs additional permissions. Please re-authenticate in connector settings.",
+                        }
+                    raise
 
-            kb_message_suffix = ""
-            try:
-                from app.services.gmail import GmailKBSyncService
+                logger.info(f"Gmail draft created: id={created.get('id')}")
 
-                kb_service = GmailKBSyncService(db_session)
-                draft_message = created.get("message", {})
-                kb_result = await kb_service.sync_after_create(
-                    message_id=draft_message.get("id", ""),
-                    thread_id=draft_message.get("threadId", ""),
-                    subject=final_subject,
-                    sender="me",
-                    date_str=datetime.now().strftime("%Y-%m-%d %H:%M:%S"),
-                    body_text=final_body,
-                    connector_id=actual_connector_id,
-                    search_space_id=search_space_id,
-                    user_id=user_id,
-                    draft_id=created.get("id"),
-                )
-                if kb_result["status"] == "success":
-                    kb_message_suffix = " Your knowledge base has also been updated."
-                else:
+                kb_message_suffix = ""
+                try:
+                    from app.services.gmail import GmailKBSyncService
+
+                    kb_service = GmailKBSyncService(db_session)
+                    draft_message = created.get("message", {})
+                    kb_result = await kb_service.sync_after_create(
+                        message_id=draft_message.get("id", ""),
+                        thread_id=draft_message.get("threadId", ""),
+                        subject=final_subject,
+                        sender="me",
+                        date_str=datetime.now().strftime("%Y-%m-%d %H:%M:%S"),
+                        body_text=final_body,
+                        connector_id=actual_connector_id,
+                        search_space_id=search_space_id,
+                        user_id=user_id,
+                        draft_id=created.get("id"),
+                    )
+                    if kb_result["status"] == "success":
+                        kb_message_suffix = (
+                            " Your knowledge base has also been updated."
+                        )
+                    else:
+                        kb_message_suffix = " This draft will be added to your knowledge base in the next scheduled sync."
+                except Exception as kb_err:
+                    logger.warning(f"KB sync after create failed: {kb_err}")
                     kb_message_suffix = " This draft will be added to your knowledge base in the next scheduled sync."
-            except Exception as kb_err:
-                logger.warning(f"KB sync after create failed: {kb_err}")
-                kb_message_suffix = " This draft will be added to your knowledge base in the next scheduled sync."
 
-            return {
-                "status": "success",
-                "draft_id": created.get("id"),
-                "message": f"Successfully created Gmail draft with subject '{final_subject}'.{kb_message_suffix}",
-            }
+                return {
+                    "status": "success",
+                    "draft_id": created.get("id"),
+                    "message": f"Successfully created Gmail draft with subject '{final_subject}'.{kb_message_suffix}",
+                }
 
         except Exception as e:
             from langgraph.errors import GraphInterrupt

surfsense_backend/app/agents/new_chat/tools/gmail/read_email.py

@@ -5,7 +5,7 @@ from langchain_core.tools import tool
 from sqlalchemy.ext.asyncio import AsyncSession
 from sqlalchemy.future import select
 
-from app.db import SearchSourceConnector, SearchSourceConnectorType
+from app.db import SearchSourceConnector, SearchSourceConnectorType, async_session_maker
 
 logger = logging.getLogger(__name__)
 
@@ -20,6 +20,23 @@ def create_read_gmail_email_tool(
     search_space_id: int | None = None,
     user_id: str | None = None,
 ):
+    """
+    Factory function to create the read_gmail_email tool.
+
+    The tool acquires its own short-lived ``AsyncSession`` per call via
+    :data:`async_session_maker` so the closure is safe to share across
+    HTTP requests by the compiled-agent cache. Capturing a per-request
+    session here would surface stale/closed sessions on cache hits.
+
+    Args:
+        db_session: Reserved for registry compatibility. Per-call sessions
+            are opened via :data:`async_session_maker` inside the tool body.
+
+    Returns:
+        Configured read_gmail_email tool
+    """
+    del db_session  # per-call session — see docstring
+
     @tool
     async def read_gmail_email(message_id: str) -> dict[str, Any]:
         """Read the full content of a specific Gmail email by its message ID.
@@ -32,108 +49,115 @@ def create_read_gmail_email_tool(
         Returns:
             Dictionary with status and the full email content formatted as markdown.
         """
-        if db_session is None or search_space_id is None or user_id is None:
+        if search_space_id is None or user_id is None:
             return {"status": "error", "message": "Gmail tool not properly configured."}
 
         try:
-            result = await db_session.execute(
-                select(SearchSourceConnector).filter(
-                    SearchSourceConnector.search_space_id == search_space_id,
-                    SearchSourceConnector.user_id == user_id,
-                    SearchSourceConnector.connector_type.in_(_GMAIL_TYPES),
+            async with async_session_maker() as db_session:
+                result = await db_session.execute(
+                    select(SearchSourceConnector).filter(
+                        SearchSourceConnector.search_space_id == search_space_id,
+                        SearchSourceConnector.user_id == user_id,
+                        SearchSourceConnector.connector_type.in_(_GMAIL_TYPES),
+                    )
                 )
-            )
-            connector = result.scalars().first()
-            if not connector:
-                return {
-                    "status": "error",
-                    "message": "No Gmail connector found. Please connect Gmail in your workspace settings.",
-                }
-
-            if (
-                connector.connector_type
-                == SearchSourceConnectorType.COMPOSIO_GMAIL_CONNECTOR
-            ):
-                cca_id = connector.config.get("composio_connected_account_id")
-                if not cca_id:
+                connector = result.scalars().first()
+                if not connector:
                     return {
                         "status": "error",
-                        "message": "Composio connected account ID not found.",
+                        "message": "No Gmail connector found. Please connect Gmail in your workspace settings.",
+                    }
+
+                if (
+                    connector.connector_type
+                    == SearchSourceConnectorType.COMPOSIO_GMAIL_CONNECTOR
+                ):
+                    cca_id = connector.config.get("composio_connected_account_id")
+                    if not cca_id:
+                        return {
+                            "status": "error",
+                            "message": "Composio connected account ID not found.",
+                        }
+
+                    from app.agents.new_chat.tools.gmail.search_emails import (
+                        _format_gmail_summary,
+                    )
+                    from app.services.composio_service import ComposioService
+
+                    service = ComposioService()
+                    detail, error = await service.get_gmail_message_detail(
+                        connected_account_id=cca_id,
+                        entity_id=f"surfsense_{user_id}",
+                        message_id=message_id,
+                    )
+                    if error:
+                        return {"status": "error", "message": error}
+                    if not detail:
+                        return {
+                            "status": "not_found",
+                            "message": f"Email with ID '{message_id}' not found.",
+                        }
+
+                    summary = _format_gmail_summary(detail)
+                    content = (
+                        f"# {summary['subject']}\n\n"
+                        f"**From:** {summary['from']}\n"
+                        f"**To:** {summary['to']}\n"
+                        f"**Date:** {summary['date']}\n\n"
+                        f"## Message Content\n\n"
+                        f"{detail.get('messageText') or detail.get('snippet') or ''}\n\n"
+                        f"## Message Details\n\n"
+                        f"- **Message ID:** {summary['message_id']}\n"
+                        f"- **Thread ID:** {summary['thread_id']}\n"
+                    )
+                    return {
+                        "status": "success",
+                        "message_id": summary["message_id"] or message_id,
+                        "content": content,
                     }
 
                 from app.agents.new_chat.tools.gmail.search_emails import (
-                    _format_gmail_summary,
+                    _build_credentials,
                 )
-                from app.services.composio_service import ComposioService
 
-                service = ComposioService()
-                detail, error = await service.get_gmail_message_detail(
-                    connected_account_id=cca_id,
-                    entity_id=f"surfsense_{user_id}",
-                    message_id=message_id,
+                creds = _build_credentials(connector)
+
+                from app.connectors.google_gmail_connector import GoogleGmailConnector
+
+                gmail = GoogleGmailConnector(
+                    credentials=creds,
+                    session=db_session,
+                    user_id=user_id,
+                    connector_id=connector.id,
                 )
+
+                detail, error = await gmail.get_message_details(message_id)
                 if error:
+                    if (
+                        "re-authenticate" in error.lower()
+                        or "authentication failed" in error.lower()
+                    ):
+                        return {
+                            "status": "auth_error",
+                            "message": error,
+                            "connector_type": "gmail",
+                        }
                     return {"status": "error", "message": error}
+
                 if not detail:
                     return {
                         "status": "not_found",
                         "message": f"Email with ID '{message_id}' not found.",
                     }
 
-                summary = _format_gmail_summary(detail)
-                content = (
-                    f"# {summary['subject']}\n\n"
-                    f"**From:** {summary['from']}\n"
-                    f"**To:** {summary['to']}\n"
-                    f"**Date:** {summary['date']}\n\n"
-                    f"## Message Content\n\n"
-                    f"{detail.get('messageText') or detail.get('snippet') or ''}\n\n"
-                    f"## Message Details\n\n"
-                    f"- **Message ID:** {summary['message_id']}\n"
-                    f"- **Thread ID:** {summary['thread_id']}\n"
-                )
+                content = gmail.format_message_to_markdown(detail)
+
                 return {
                     "status": "success",
-                    "message_id": summary["message_id"] or message_id,
+                    "message_id": message_id,
                     "content": content,
                 }
 
-            from app.agents.new_chat.tools.gmail.search_emails import _build_credentials
-
-            creds = _build_credentials(connector)
-
-            from app.connectors.google_gmail_connector import GoogleGmailConnector
-
-            gmail = GoogleGmailConnector(
-                credentials=creds,
-                session=db_session,
-                user_id=user_id,
-                connector_id=connector.id,
-            )
-
-            detail, error = await gmail.get_message_details(message_id)
-            if error:
-                if (
-                    "re-authenticate" in error.lower()
-                    or "authentication failed" in error.lower()
-                ):
-                    return {
-                        "status": "auth_error",
-                        "message": error,
-                        "connector_type": "gmail",
-                    }
-                return {"status": "error", "message": error}
-
-            if not detail:
-                return {
-                    "status": "not_found",
-                    "message": f"Email with ID '{message_id}' not found.",
-                }
-
-            content = gmail.format_message_to_markdown(detail)
-
-            return {"status": "success", "message_id": message_id, "content": content}
-
         except Exception as e:
             from langgraph.errors import GraphInterrupt
 

surfsense_backend/app/agents/new_chat/tools/gmail/search_emails.py

@@ -6,7 +6,7 @@ from langchain_core.tools import tool
 from sqlalchemy.ext.asyncio import AsyncSession
 from sqlalchemy.future import select
 
-from app.db import SearchSourceConnector, SearchSourceConnectorType
+from app.db import SearchSourceConnector, SearchSourceConnectorType, async_session_maker
 
 logger = logging.getLogger(__name__)
 
@@ -124,6 +124,23 @@ def create_search_gmail_tool(
     search_space_id: int | None = None,
     user_id: str | None = None,
 ):
+    """
+    Factory function to create the search_gmail tool.
+
+    The tool acquires its own short-lived ``AsyncSession`` per call via
+    :data:`async_session_maker` so the closure is safe to share across
+    HTTP requests by the compiled-agent cache. Capturing a per-request
+    session here would surface stale/closed sessions on cache hits.
+
+    Args:
+        db_session: Reserved for registry compatibility. Per-call sessions
+            are opened via :data:`async_session_maker` inside the tool body.
+
+    Returns:
+        Configured search_gmail tool
+    """
+    del db_session  # per-call session — see docstring
+
     @tool
     async def search_gmail(
         query: str,
@@ -142,91 +159,92 @@ def create_search_gmail_tool(
             Dictionary with status and a list of email summaries including
             message_id, subject, from, date, snippet.
         """
-        if db_session is None or search_space_id is None or user_id is None:
+        if search_space_id is None or user_id is None:
             return {"status": "error", "message": "Gmail tool not properly configured."}
 
         max_results = min(max_results, 20)
 
         try:
-            result = await db_session.execute(
-                select(SearchSourceConnector).filter(
-                    SearchSourceConnector.search_space_id == search_space_id,
-                    SearchSourceConnector.user_id == user_id,
-                    SearchSourceConnector.connector_type.in_(_GMAIL_TYPES),
+            async with async_session_maker() as db_session:
+                result = await db_session.execute(
+                    select(SearchSourceConnector).filter(
+                        SearchSourceConnector.search_space_id == search_space_id,
+                        SearchSourceConnector.user_id == user_id,
+                        SearchSourceConnector.connector_type.in_(_GMAIL_TYPES),
+                    )
                 )
-            )
-            connector = result.scalars().first()
-            if not connector:
-                return {
-                    "status": "error",
-                    "message": "No Gmail connector found. Please connect Gmail in your workspace settings.",
-                }
-
-            if (
-                connector.connector_type
-                == SearchSourceConnectorType.COMPOSIO_GMAIL_CONNECTOR
-            ):
-                return await _search_composio_gmail(
-                    connector, str(user_id), query, max_results
-                )
-
-            creds = _build_credentials(connector)
-
-            from app.connectors.google_gmail_connector import GoogleGmailConnector
-
-            gmail = GoogleGmailConnector(
-                credentials=creds,
-                session=db_session,
-                user_id=user_id,
-                connector_id=connector.id,
-            )
-
-            messages_list, error = await gmail.get_messages_list(
-                max_results=max_results, query=query
-            )
-            if error:
-                if (
-                    "re-authenticate" in error.lower()
-                    or "authentication failed" in error.lower()
-                ):
+                connector = result.scalars().first()
+                if not connector:
                     return {
-                        "status": "auth_error",
-                        "message": error,
-                        "connector_type": "gmail",
+                        "status": "error",
+                        "message": "No Gmail connector found. Please connect Gmail in your workspace settings.",
                     }
-                return {"status": "error", "message": error}
 
-            if not messages_list:
-                return {
-                    "status": "success",
-                    "emails": [],
-                    "total": 0,
-                    "message": "No emails found.",
-                }
+                if (
+                    connector.connector_type
+                    == SearchSourceConnectorType.COMPOSIO_GMAIL_CONNECTOR
+                ):
+                    return await _search_composio_gmail(
+                        connector, str(user_id), query, max_results
+                    )
 
-            emails = []
-            for msg in messages_list:
-                detail, err = await gmail.get_message_details(msg["id"])
-                if err:
-                    continue
-                headers = {
-                    h["name"].lower(): h["value"]
-                    for h in detail.get("payload", {}).get("headers", [])
-                }
-                emails.append(
-                    {
-                        "message_id": detail.get("id"),
-                        "thread_id": detail.get("threadId"),
-                        "subject": headers.get("subject", "No Subject"),
-                        "from": headers.get("from", "Unknown"),
-                        "to": headers.get("to", ""),
-                        "date": headers.get("date", ""),
-                        "snippet": detail.get("snippet", ""),
-                        "labels": detail.get("labelIds", []),
-                    }
+                creds = _build_credentials(connector)
+
+                from app.connectors.google_gmail_connector import GoogleGmailConnector
+
+                gmail = GoogleGmailConnector(
+                    credentials=creds,
+                    session=db_session,
+                    user_id=user_id,
+                    connector_id=connector.id,
                 )
 
-            return {"status": "success", "emails": emails, "total": len(emails)}
+                messages_list, error = await gmail.get_messages_list(
+                    max_results=max_results, query=query
+                )
+                if error:
+                    if (
+                        "re-authenticate" in error.lower()
+                        or "authentication failed" in error.lower()
+                    ):
+                        return {
+                            "status": "auth_error",
+                            "message": error,
+                            "connector_type": "gmail",
+                        }
+                    return {"status": "error", "message": error}
+
+                if not messages_list:
+                    return {
+                        "status": "success",
+                        "emails": [],
+                        "total": 0,
+                        "message": "No emails found.",
+                    }
+
+                emails = []
+                for msg in messages_list:
+                    detail, err = await gmail.get_message_details(msg["id"])
+                    if err:
+                        continue
+                    headers = {
+                        h["name"].lower(): h["value"]
+                        for h in detail.get("payload", {}).get("headers", [])
+                    }
+                    emails.append(
+                        {
+                            "message_id": detail.get("id"),
+                            "thread_id": detail.get("threadId"),
+                            "subject": headers.get("subject", "No Subject"),
+                            "from": headers.get("from", "Unknown"),
+                            "to": headers.get("to", ""),
+                            "date": headers.get("date", ""),
+                            "snippet": detail.get("snippet", ""),
+                            "labels": detail.get("labelIds", []),
+                        }
+                    )
+
+                return {"status": "success", "emails": emails, "total": len(emails)}
 
         except Exception as e:
             from langgraph.errors import GraphInterrupt

surfsense_backend/app/agents/new_chat/tools/gmail/send_email.py

@@ -9,6 +9,7 @@ from langchain_core.tools import tool
 from sqlalchemy.ext.asyncio import AsyncSession
 
 from app.agents.new_chat.tools.hitl import request_approval
+from app.db import async_session_maker
 from app.services.gmail import GmailToolMetadataService
 
 logger = logging.getLogger(__name__)
@@ -19,6 +20,23 @@ def create_send_gmail_email_tool(
     search_space_id: int | None = None,
     user_id: str | None = None,
 ):
+    """
+    Factory function to create the send_gmail_email tool.
+
+    The tool acquires its own short-lived ``AsyncSession`` per call via
+    :data:`async_session_maker` so the closure is safe to share across
+    HTTP requests by the compiled-agent cache. Capturing a per-request
+    session here would surface stale/closed sessions on cache hits.
+
+    Args:
+        db_session: Reserved for registry compatibility. Per-call sessions
+            are opened via :data:`async_session_maker` inside the tool body.
+
+    Returns:
+        Configured send_gmail_email tool
+    """
+    del db_session  # per-call session — see docstring
+
     @tool
     async def send_gmail_email(
         to: str,
@@ -58,268 +76,277 @@ def create_send_gmail_email_tool(
         """
         logger.info(f"send_gmail_email called: to='{to}', subject='{subject}'")
 
-        if db_session is None or search_space_id is None or user_id is None:
+        if search_space_id is None or user_id is None:
             return {
                 "status": "error",
                 "message": "Gmail tool not properly configured. Please contact support.",
             }
 
         try:
-            metadata_service = GmailToolMetadataService(db_session)
-            context = await metadata_service.get_creation_context(
-                search_space_id, user_id
-            )
+            async with async_session_maker() as db_session:
+                metadata_service = GmailToolMetadataService(db_session)
+                context = await metadata_service.get_creation_context(
+                    search_space_id, user_id
+                )
 
-            if "error" in context:
-                logger.error(f"Failed to fetch creation context: {context['error']}")
-                return {"status": "error", "message": context["error"]}
-
-            accounts = context.get("accounts", [])
-            if accounts and all(a.get("auth_expired") for a in accounts):
-                logger.warning("All Gmail accounts have expired authentication")
-                return {
-                    "status": "auth_error",
-                    "message": "All connected Gmail accounts need re-authentication. Please re-authenticate in your connector settings.",
-                    "connector_type": "gmail",
-                }
-
-            logger.info(
-                f"Requesting approval for sending Gmail email: to='{to}', subject='{subject}'"
-            )
-            result = request_approval(
-                action_type="gmail_email_send",
-                tool_name="send_gmail_email",
-                params={
-                    "to": to,
-                    "subject": subject,
-                    "body": body,
-                    "cc": cc,
-                    "bcc": bcc,
-                    "connector_id": None,
-                },
-                context=context,
-            )
-
-            if result.rejected:
-                return {
-                    "status": "rejected",
-                    "message": "User declined. The email was not sent. Do not ask again or suggest alternatives.",
-                }
-
-            final_to = result.params.get("to", to)
-            final_subject = result.params.get("subject", subject)
-            final_body = result.params.get("body", body)
-            final_cc = result.params.get("cc", cc)
-            final_bcc = result.params.get("bcc", bcc)
-            final_connector_id = result.params.get("connector_id")
-
-            from sqlalchemy.future import select
-
-            from app.db import SearchSourceConnector, SearchSourceConnectorType
-
-            _gmail_types = [
-                SearchSourceConnectorType.GOOGLE_GMAIL_CONNECTOR,
-                SearchSourceConnectorType.COMPOSIO_GMAIL_CONNECTOR,
-            ]
-
-            if final_connector_id is not None:
-                result = await db_session.execute(
-                    select(SearchSourceConnector).filter(
-                        SearchSourceConnector.id == final_connector_id,
-                        SearchSourceConnector.search_space_id == search_space_id,
-                        SearchSourceConnector.user_id == user_id,
-                        SearchSourceConnector.connector_type.in_(_gmail_types),
+                if "error" in context:
+                    logger.error(
+                        f"Failed to fetch creation context: {context['error']}"
                     )
-                )
-                connector = result.scalars().first()
-                if not connector:
+                    return {"status": "error", "message": context["error"]}
+
+                accounts = context.get("accounts", [])
+                if accounts and all(a.get("auth_expired") for a in accounts):
+                    logger.warning("All Gmail accounts have expired authentication")
                     return {
-                        "status": "error",
-                        "message": "Selected Gmail connector is invalid or has been disconnected.",
+                        "status": "auth_error",
+                        "message": "All connected Gmail accounts need re-authentication. Please re-authenticate in your connector settings.",
+                        "connector_type": "gmail",
                     }
-                actual_connector_id = connector.id
-            else:
-                result = await db_session.execute(
-                    select(SearchSourceConnector).filter(
-                        SearchSourceConnector.search_space_id == search_space_id,
-                        SearchSourceConnector.user_id == user_id,
-                        SearchSourceConnector.connector_type.in_(_gmail_types),
+
+                logger.info(
+                    f"Requesting approval for sending Gmail email: to='{to}', subject='{subject}'"
+                )
+                result = request_approval(
+                    action_type="gmail_email_send",
+                    tool_name="send_gmail_email",
+                    params={
+                        "to": to,
+                        "subject": subject,
+                        "body": body,
+                        "cc": cc,
+                        "bcc": bcc,
+                        "connector_id": None,
+                    },
+                    context=context,
+                )
+
+                if result.rejected:
+                    return {
+                        "status": "rejected",
+                        "message": "User declined. The email was not sent. Do not ask again or suggest alternatives.",
+                    }
+
+                final_to = result.params.get("to", to)
+                final_subject = result.params.get("subject", subject)
+                final_body = result.params.get("body", body)
+                final_cc = result.params.get("cc", cc)
+                final_bcc = result.params.get("bcc", bcc)
+                final_connector_id = result.params.get("connector_id")
+
+                from sqlalchemy.future import select
+
+                from app.db import SearchSourceConnector, SearchSourceConnectorType
+
+                _gmail_types = [
+                    SearchSourceConnectorType.GOOGLE_GMAIL_CONNECTOR,
+                    SearchSourceConnectorType.COMPOSIO_GMAIL_CONNECTOR,
+                ]
+
+                if final_connector_id is not None:
+                    result = await db_session.execute(
+                        select(SearchSourceConnector).filter(
+                            SearchSourceConnector.id == final_connector_id,
+                            SearchSourceConnector.search_space_id == search_space_id,
+                            SearchSourceConnector.user_id == user_id,
+                            SearchSourceConnector.connector_type.in_(_gmail_types),
+                        )
                     )
-                )
-                connector = result.scalars().first()
-                if not connector:
-                    return {
-                        "status": "error",
-                        "message": "No Gmail connector found. Please connect Gmail in your workspace settings.",
-                    }
-                actual_connector_id = connector.id
-
-            logger.info(
-                f"Sending Gmail email: to='{final_to}', subject='{final_subject}', connector={actual_connector_id}"
-            )
-
-            is_composio_gmail = (
-                connector.connector_type
-                == SearchSourceConnectorType.COMPOSIO_GMAIL_CONNECTOR
-            )
-            if is_composio_gmail:
-                cca_id = connector.config.get("composio_connected_account_id")
-                if not cca_id:
-                    return {
-                        "status": "error",
-                        "message": "Composio connected account ID not found for this Gmail connector.",
-                    }
-            else:
-                from google.oauth2.credentials import Credentials
-
-                from app.config import config
-                from app.utils.oauth_security import TokenEncryption
-
-                config_data = dict(connector.config)
-                token_encrypted = config_data.get("_token_encrypted", False)
-                if token_encrypted and config.SECRET_KEY:
-                    token_encryption = TokenEncryption(config.SECRET_KEY)
-                    if config_data.get("token"):
-                        config_data["token"] = token_encryption.decrypt_token(
-                            config_data["token"]
-                        )
-                    if config_data.get("refresh_token"):
-                        config_data["refresh_token"] = token_encryption.decrypt_token(
-                            config_data["refresh_token"]
-                        )
-                    if config_data.get("client_secret"):
-                        config_data["client_secret"] = token_encryption.decrypt_token(
-                            config_data["client_secret"]
+                    connector = result.scalars().first()
+                    if not connector:
+                        return {
+                            "status": "error",
+                            "message": "Selected Gmail connector is invalid or has been disconnected.",
+                        }
+                    actual_connector_id = connector.id
+                else:
+                    result = await db_session.execute(
+                        select(SearchSourceConnector).filter(
+                            SearchSourceConnector.search_space_id == search_space_id,
+                            SearchSourceConnector.user_id == user_id,
+                            SearchSourceConnector.connector_type.in_(_gmail_types),
                         )
+                    )
+                    connector = result.scalars().first()
+                    if not connector:
+                        return {
+                            "status": "error",
+                            "message": "No Gmail connector found. Please connect Gmail in your workspace settings.",
+                        }
+                    actual_connector_id = connector.id
 
-                exp = config_data.get("expiry", "")
-                if exp:
-                    exp = exp.replace("Z", "")
-
-                creds = Credentials(
-                    token=config_data.get("token"),
-                    refresh_token=config_data.get("refresh_token"),
-                    token_uri=config_data.get("token_uri"),
-                    client_id=config_data.get("client_id"),
-                    client_secret=config_data.get("client_secret"),
-                    scopes=config_data.get("scopes", []),
-                    expiry=datetime.fromisoformat(exp) if exp else None,
+                logger.info(
+                    f"Sending Gmail email: to='{final_to}', subject='{final_subject}', connector={actual_connector_id}"
                 )
 
-            message = MIMEText(final_body)
-            message["to"] = final_to
-            message["subject"] = final_subject
-            if final_cc:
-                message["cc"] = final_cc
-            if final_bcc:
-                message["bcc"] = final_bcc
-            raw = base64.urlsafe_b64encode(message.as_bytes()).decode()
-
-            try:
+                is_composio_gmail = (
+                    connector.connector_type
+                    == SearchSourceConnectorType.COMPOSIO_GMAIL_CONNECTOR
+                )
                 if is_composio_gmail:
-                    from app.agents.new_chat.tools.gmail.composio_helpers import (
-                        execute_composio_gmail_tool,
-                        split_recipients,
-                    )
-
-                    sent, error = await execute_composio_gmail_tool(
-                        connector,
-                        user_id,
-                        "GMAIL_SEND_EMAIL",
-                        {
-                            "user_id": "me",
-                            "recipient_email": final_to,
-                            "subject": final_subject,
-                            "body": final_body,
-                            "cc": split_recipients(final_cc),
-                            "bcc": split_recipients(final_bcc),
-                            "is_html": False,
-                        },
-                    )
-                    if error:
-                        raise RuntimeError(error)
-                    if not isinstance(sent, dict):
-                        sent = {}
+                    cca_id = connector.config.get("composio_connected_account_id")
+                    if not cca_id:
+                        return {
+                            "status": "error",
+                            "message": "Composio connected account ID not found for this Gmail connector.",
+                        }
                 else:
-                    from googleapiclient.discovery import build
+                    from google.oauth2.credentials import Credentials
 
-                    gmail_service = build("gmail", "v1", credentials=creds)
-                    sent = await asyncio.get_event_loop().run_in_executor(
-                        None,
-                        lambda: (
-                            gmail_service.users()
-                            .messages()
-                            .send(userId="me", body={"raw": raw})
-                            .execute()
-                        ),
-                    )
-            except Exception as api_err:
-                from googleapiclient.errors import HttpError
+                    from app.config import config
+                    from app.utils.oauth_security import TokenEncryption
 
-                if isinstance(api_err, HttpError) and api_err.resp.status == 403:
-                    logger.warning(
-                        f"Insufficient permissions for connector {actual_connector_id}: {api_err}"
-                    )
-                    try:
-                        from sqlalchemy.orm.attributes import flag_modified
-
-                        _res = await db_session.execute(
-                            select(SearchSourceConnector).where(
-                                SearchSourceConnector.id == actual_connector_id
+                    config_data = dict(connector.config)
+                    token_encrypted = config_data.get("_token_encrypted", False)
+                    if token_encrypted and config.SECRET_KEY:
+                        token_encryption = TokenEncryption(config.SECRET_KEY)
+                        if config_data.get("token"):
+                            config_data["token"] = token_encryption.decrypt_token(
+                                config_data["token"]
                             )
+                        if config_data.get("refresh_token"):
+                            config_data["refresh_token"] = (
+                                token_encryption.decrypt_token(
+                                    config_data["refresh_token"]
+                                )
+                            )
+                        if config_data.get("client_secret"):
+                            config_data["client_secret"] = (
+                                token_encryption.decrypt_token(
+                                    config_data["client_secret"]
+                                )
+                            )
+
+                    exp = config_data.get("expiry", "")
+                    if exp:
+                        exp = exp.replace("Z", "")
+
+                    creds = Credentials(
+                        token=config_data.get("token"),
+                        refresh_token=config_data.get("refresh_token"),
+                        token_uri=config_data.get("token_uri"),
+                        client_id=config_data.get("client_id"),
+                        client_secret=config_data.get("client_secret"),
+                        scopes=config_data.get("scopes", []),
+                        expiry=datetime.fromisoformat(exp) if exp else None,
+                    )
+
+                message = MIMEText(final_body)
+                message["to"] = final_to
+                message["subject"] = final_subject
+                if final_cc:
+                    message["cc"] = final_cc
+                if final_bcc:
+                    message["bcc"] = final_bcc
+                raw = base64.urlsafe_b64encode(message.as_bytes()).decode()
+
+                try:
+                    if is_composio_gmail:
+                        from app.agents.new_chat.tools.gmail.composio_helpers import (
+                            execute_composio_gmail_tool,
+                            split_recipients,
                         )
-                        _conn = _res.scalar_one_or_none()
-                        if _conn and not _conn.config.get("auth_expired"):
-                            _conn.config = {**_conn.config, "auth_expired": True}
-                            flag_modified(_conn, "config")
-                            await db_session.commit()
-                    except Exception:
+
+                        sent, error = await execute_composio_gmail_tool(
+                            connector,
+                            user_id,
+                            "GMAIL_SEND_EMAIL",
+                            {
+                                "user_id": "me",
+                                "recipient_email": final_to,
+                                "subject": final_subject,
+                                "body": final_body,
+                                "cc": split_recipients(final_cc),
+                                "bcc": split_recipients(final_bcc),
+                                "is_html": False,
+                            },
+                        )
+                        if error:
+                            raise RuntimeError(error)
+                        if not isinstance(sent, dict):
+                            sent = {}
+                    else:
+                        from googleapiclient.discovery import build
+
+                        gmail_service = build("gmail", "v1", credentials=creds)
+                        sent = await asyncio.get_event_loop().run_in_executor(
+                            None,
+                            lambda: (
+                                gmail_service.users()
+                                .messages()
+                                .send(userId="me", body={"raw": raw})
+                                .execute()
+                            ),
+                        )
+                except Exception as api_err:
+                    from googleapiclient.errors import HttpError
+
+                    if isinstance(api_err, HttpError) and api_err.resp.status == 403:
                         logger.warning(
-                            "Failed to persist auth_expired for connector %s",
-                            actual_connector_id,
-                            exc_info=True,
+                            f"Insufficient permissions for connector {actual_connector_id}: {api_err}"
                         )
-                    return {
-                        "status": "insufficient_permissions",
-                        "connector_id": actual_connector_id,
-                        "message": "This Gmail account needs additional permissions. Please re-authenticate in connector settings.",
-                    }
-                raise
+                        try:
+                            from sqlalchemy.orm.attributes import flag_modified
 
-            logger.info(
-                f"Gmail email sent: id={sent.get('id')}, threadId={sent.get('threadId')}"
-            )
+                            _res = await db_session.execute(
+                                select(SearchSourceConnector).where(
+                                    SearchSourceConnector.id == actual_connector_id
+                                )
+                            )
+                            _conn = _res.scalar_one_or_none()
+                            if _conn and not _conn.config.get("auth_expired"):
+                                _conn.config = {**_conn.config, "auth_expired": True}
+                                flag_modified(_conn, "config")
+                                await db_session.commit()
+                        except Exception:
+                            logger.warning(
+                                "Failed to persist auth_expired for connector %s",
+                                actual_connector_id,
+                                exc_info=True,
+                            )
+                        return {
+                            "status": "insufficient_permissions",
+                            "connector_id": actual_connector_id,
+                            "message": "This Gmail account needs additional permissions. Please re-authenticate in connector settings.",
+                        }
+                    raise
 
-            kb_message_suffix = ""
-            try:
-                from app.services.gmail import GmailKBSyncService
-
-                kb_service = GmailKBSyncService(db_session)
-                kb_result = await kb_service.sync_after_create(
-                    message_id=sent.get("id", ""),
-                    thread_id=sent.get("threadId", ""),
-                    subject=final_subject,
-                    sender="me",
-                    date_str=datetime.now().strftime("%Y-%m-%d %H:%M:%S"),
-                    body_text=final_body,
-                    connector_id=actual_connector_id,
-                    search_space_id=search_space_id,
-                    user_id=user_id,
+                logger.info(
+                    f"Gmail email sent: id={sent.get('id')}, threadId={sent.get('threadId')}"
                 )
-                if kb_result["status"] == "success":
-                    kb_message_suffix = " Your knowledge base has also been updated."
-                else:
-                    kb_message_suffix = " This email will be added to your knowledge base in the next scheduled sync."
-            except Exception as kb_err:
-                logger.warning(f"KB sync after send failed: {kb_err}")
-                kb_message_suffix = " This email will be added to your knowledge base in the next scheduled sync."
 
-            return {
-                "status": "success",
-                "message_id": sent.get("id"),
-                "thread_id": sent.get("threadId"),
-                "message": f"Successfully sent email to '{final_to}' with subject '{final_subject}'.{kb_message_suffix}",
-            }
+                kb_message_suffix = ""
+                try:
+                    from app.services.gmail import GmailKBSyncService
+
+                    kb_service = GmailKBSyncService(db_session)
+                    kb_result = await kb_service.sync_after_create(
+                        message_id=sent.get("id", ""),
+                        thread_id=sent.get("threadId", ""),
+                        subject=final_subject,
+                        sender="me",
+                        date_str=datetime.now().strftime("%Y-%m-%d %H:%M:%S"),
+                        body_text=final_body,
+                        connector_id=actual_connector_id,
+                        search_space_id=search_space_id,
+                        user_id=user_id,
+                    )
+                    if kb_result["status"] == "success":
+                        kb_message_suffix = (
+                            " Your knowledge base has also been updated."
+                        )
+                    else:
+                        kb_message_suffix = " This email will be added to your knowledge base in the next scheduled sync."
+                except Exception as kb_err:
+                    logger.warning(f"KB sync after send failed: {kb_err}")
+                    kb_message_suffix = " This email will be added to your knowledge base in the next scheduled sync."
+
+                return {
+                    "status": "success",
+                    "message_id": sent.get("id"),
+                    "thread_id": sent.get("threadId"),
+                    "message": f"Successfully sent email to '{final_to}' with subject '{final_subject}'.{kb_message_suffix}",
+                }
 
         except Exception as e:
             from langgraph.errors import GraphInterrupt

surfsense_backend/app/agents/new_chat/tools/gmail/trash_email.py

@@ -7,6 +7,7 @@ from langchain_core.tools import tool
 from sqlalchemy.ext.asyncio import AsyncSession
 
 from app.agents.new_chat.tools.hitl import request_approval
+from app.db import async_session_maker
 from app.services.gmail import GmailToolMetadataService
 
 logger = logging.getLogger(__name__)
@@ -17,6 +18,23 @@ def create_trash_gmail_email_tool(
     search_space_id: int | None = None,
     user_id: str | None = None,
 ):
+    """
+    Factory function to create the trash_gmail_email tool.
+
+    The tool acquires its own short-lived ``AsyncSession`` per call via
+    :data:`async_session_maker` so the closure is safe to share across
+    HTTP requests by the compiled-agent cache. Capturing a per-request
+    session here would surface stale/closed sessions on cache hits.
+
+    Args:
+        db_session: Reserved for registry compatibility. Per-call sessions
+            are opened via :data:`async_session_maker` inside the tool body.
+
+    Returns:
+        Configured trash_gmail_email tool
+    """
+    del db_session  # per-call session — see docstring
+
     @tool
     async def trash_gmail_email(
         email_subject_or_id: str,
@@ -55,254 +73,261 @@ def create_trash_gmail_email_tool(
             f"trash_gmail_email called: email_subject_or_id='{email_subject_or_id}', delete_from_kb={delete_from_kb}"
         )
 
-        if db_session is None or search_space_id is None or user_id is None:
+        if search_space_id is None or user_id is None:
             return {
                 "status": "error",
                 "message": "Gmail tool not properly configured. Please contact support.",
             }
 
         try:
-            metadata_service = GmailToolMetadataService(db_session)
-            context = await metadata_service.get_trash_context(
-                search_space_id, user_id, email_subject_or_id
-            )
-
-            if "error" in context:
-                error_msg = context["error"]
-                if "not found" in error_msg.lower():
-                    logger.warning(f"Email not found: {error_msg}")
-                    return {"status": "not_found", "message": error_msg}
-                logger.error(f"Failed to fetch trash context: {error_msg}")
-                return {"status": "error", "message": error_msg}
-
-            account = context.get("account", {})
-            if account.get("auth_expired"):
-                logger.warning(
-                    "Gmail account %s has expired authentication",
-                    account.get("id"),
+            async with async_session_maker() as db_session:
+                metadata_service = GmailToolMetadataService(db_session)
+                context = await metadata_service.get_trash_context(
+                    search_space_id, user_id, email_subject_or_id
                 )
-                return {
-                    "status": "auth_error",
-                    "message": "The Gmail account for this email needs re-authentication. Please re-authenticate in your connector settings.",
-                    "connector_type": "gmail",
-                }
 
-            email = context["email"]
-            message_id = email["message_id"]
-            document_id = email.get("document_id")
-            connector_id_from_context = context["account"]["id"]
+                if "error" in context:
+                    error_msg = context["error"]
+                    if "not found" in error_msg.lower():
+                        logger.warning(f"Email not found: {error_msg}")
+                        return {"status": "not_found", "message": error_msg}
+                    logger.error(f"Failed to fetch trash context: {error_msg}")
+                    return {"status": "error", "message": error_msg}
 
-            if not message_id:
-                return {
-                    "status": "error",
-                    "message": "Message ID is missing from the indexed document. Please re-index the email and try again.",
-                }
+                account = context.get("account", {})
+                if account.get("auth_expired"):
+                    logger.warning(
+                        "Gmail account %s has expired authentication",
+                        account.get("id"),
+                    )
+                    return {
+                        "status": "auth_error",
+                        "message": "The Gmail account for this email needs re-authentication. Please re-authenticate in your connector settings.",
+                        "connector_type": "gmail",
+                    }
 
-            logger.info(
-                f"Requesting approval for trashing Gmail email: '{email_subject_or_id}' (message_id={message_id}, delete_from_kb={delete_from_kb})"
-            )
-            result = request_approval(
-                action_type="gmail_email_trash",
-                tool_name="trash_gmail_email",
-                params={
-                    "message_id": message_id,
-                    "connector_id": connector_id_from_context,
-                    "delete_from_kb": delete_from_kb,
-                },
-                context=context,
-            )
+                email = context["email"]
+                message_id = email["message_id"]
+                document_id = email.get("document_id")
+                connector_id_from_context = context["account"]["id"]
 
-            if result.rejected:
-                return {
-                    "status": "rejected",
-                    "message": "User declined. The email was not trashed. Do not ask again or suggest alternatives.",
-                }
-
-            final_message_id = result.params.get("message_id", message_id)
-            final_connector_id = result.params.get(
-                "connector_id", connector_id_from_context
-            )
-            final_delete_from_kb = result.params.get("delete_from_kb", delete_from_kb)
-
-            if not final_connector_id:
-                return {
-                    "status": "error",
-                    "message": "No connector found for this email.",
-                }
-
-            from sqlalchemy.future import select
-
-            from app.db import SearchSourceConnector, SearchSourceConnectorType
-
-            _gmail_types = [
-                SearchSourceConnectorType.GOOGLE_GMAIL_CONNECTOR,
-                SearchSourceConnectorType.COMPOSIO_GMAIL_CONNECTOR,
-            ]
-
-            result = await db_session.execute(
-                select(SearchSourceConnector).filter(
-                    SearchSourceConnector.id == final_connector_id,
-                    SearchSourceConnector.search_space_id == search_space_id,
-                    SearchSourceConnector.user_id == user_id,
-                    SearchSourceConnector.connector_type.in_(_gmail_types),
-                )
-            )
-            connector = result.scalars().first()
-            if not connector:
-                return {
-                    "status": "error",
-                    "message": "Selected Gmail connector is invalid or has been disconnected.",
-                }
-
-            logger.info(
-                f"Trashing Gmail email: message_id='{final_message_id}', connector={final_connector_id}"
-            )
-
-            is_composio_gmail = (
-                connector.connector_type
-                == SearchSourceConnectorType.COMPOSIO_GMAIL_CONNECTOR
-            )
-            if is_composio_gmail:
-                cca_id = connector.config.get("composio_connected_account_id")
-                if not cca_id:
+                if not message_id:
                     return {
                         "status": "error",
-                        "message": "Composio connected account ID not found for this Gmail connector.",
+                        "message": "Message ID is missing from the indexed document. Please re-index the email and try again.",
                     }
-            else:
-                from google.oauth2.credentials import Credentials
 
-                from app.config import config
-                from app.utils.oauth_security import TokenEncryption
-
-                config_data = dict(connector.config)
-                token_encrypted = config_data.get("_token_encrypted", False)
-                if token_encrypted and config.SECRET_KEY:
-                    token_encryption = TokenEncryption(config.SECRET_KEY)
-                    if config_data.get("token"):
-                        config_data["token"] = token_encryption.decrypt_token(
-                            config_data["token"]
-                        )
-                    if config_data.get("refresh_token"):
-                        config_data["refresh_token"] = token_encryption.decrypt_token(
-                            config_data["refresh_token"]
-                        )
-                    if config_data.get("client_secret"):
-                        config_data["client_secret"] = token_encryption.decrypt_token(
-                            config_data["client_secret"]
-                        )
-
-                exp = config_data.get("expiry", "")
-                if exp:
-                    exp = exp.replace("Z", "")
-
-                creds = Credentials(
-                    token=config_data.get("token"),
-                    refresh_token=config_data.get("refresh_token"),
-                    token_uri=config_data.get("token_uri"),
-                    client_id=config_data.get("client_id"),
-                    client_secret=config_data.get("client_secret"),
-                    scopes=config_data.get("scopes", []),
-                    expiry=datetime.fromisoformat(exp) if exp else None,
+                logger.info(
+                    f"Requesting approval for trashing Gmail email: '{email_subject_or_id}' (message_id={message_id}, delete_from_kb={delete_from_kb})"
+                )
+                result = request_approval(
+                    action_type="gmail_email_trash",
+                    tool_name="trash_gmail_email",
+                    params={
+                        "message_id": message_id,
+                        "connector_id": connector_id_from_context,
+                        "delete_from_kb": delete_from_kb,
+                    },
+                    context=context,
                 )
 
-            try:
-                if is_composio_gmail:
-                    from app.agents.new_chat.tools.gmail.composio_helpers import (
-                        execute_composio_gmail_tool,
-                    )
-
-                    _trashed, error = await execute_composio_gmail_tool(
-                        connector,
-                        user_id,
-                        "GMAIL_MOVE_TO_TRASH",
-                        {"user_id": "me", "message_id": final_message_id},
-                    )
-                    if error:
-                        raise RuntimeError(error)
-                else:
-                    from googleapiclient.discovery import build
-
-                    gmail_service = build("gmail", "v1", credentials=creds)
-                    await asyncio.get_event_loop().run_in_executor(
-                        None,
-                        lambda: (
-                            gmail_service.users()
-                            .messages()
-                            .trash(userId="me", id=final_message_id)
-                            .execute()
-                        ),
-                    )
-            except Exception as api_err:
-                from googleapiclient.errors import HttpError
-
-                if isinstance(api_err, HttpError) and api_err.resp.status == 403:
-                    logger.warning(
-                        f"Insufficient permissions for connector {connector.id}: {api_err}"
-                    )
-                    try:
-                        from sqlalchemy.orm.attributes import flag_modified
-
-                        if not connector.config.get("auth_expired"):
-                            connector.config = {
-                                **connector.config,
-                                "auth_expired": True,
-                            }
-                            flag_modified(connector, "config")
-                            await db_session.commit()
-                    except Exception:
-                        logger.warning(
-                            "Failed to persist auth_expired for connector %s",
-                            connector.id,
-                            exc_info=True,
-                        )
+                if result.rejected:
                     return {
-                        "status": "insufficient_permissions",
-                        "connector_id": connector.id,
-                        "message": "This Gmail account needs additional permissions. Please re-authenticate in connector settings.",
+                        "status": "rejected",
+                        "message": "User declined. The email was not trashed. Do not ask again or suggest alternatives.",
                     }
-                raise
 
-            logger.info(f"Gmail email trashed: message_id={final_message_id}")
-
-            trash_result: dict[str, Any] = {
-                "status": "success",
-                "message_id": final_message_id,
-                "message": f"Successfully moved email '{email.get('subject', email_subject_or_id)}' to trash.",
-            }
-
-            deleted_from_kb = False
-            if final_delete_from_kb and document_id:
-                try:
-                    from app.db import Document
-
-                    doc_result = await db_session.execute(
-                        select(Document).filter(Document.id == document_id)
-                    )
-                    document = doc_result.scalars().first()
-                    if document:
-                        await db_session.delete(document)
-                        await db_session.commit()
-                        deleted_from_kb = True
-                        logger.info(
-                            f"Deleted document {document_id} from knowledge base"
-                        )
-                    else:
-                        logger.warning(f"Document {document_id} not found in KB")
-                except Exception as e:
-                    logger.error(f"Failed to delete document from KB: {e}")
-                    await db_session.rollback()
-                    trash_result["warning"] = (
-                        f"Email trashed, but failed to remove from knowledge base: {e!s}"
-                    )
-
-            trash_result["deleted_from_kb"] = deleted_from_kb
-            if deleted_from_kb:
-                trash_result["message"] = (
-                    f"{trash_result.get('message', '')} (also removed from knowledge base)"
+                final_message_id = result.params.get("message_id", message_id)
+                final_connector_id = result.params.get(
+                    "connector_id", connector_id_from_context
+                )
+                final_delete_from_kb = result.params.get(
+                    "delete_from_kb", delete_from_kb
                 )
 
-            return trash_result
+                if not final_connector_id:
+                    return {
+                        "status": "error",
+                        "message": "No connector found for this email.",
+                    }
+
+                from sqlalchemy.future import select
+
+                from app.db import SearchSourceConnector, SearchSourceConnectorType
+
+                _gmail_types = [
+                    SearchSourceConnectorType.GOOGLE_GMAIL_CONNECTOR,
+                    SearchSourceConnectorType.COMPOSIO_GMAIL_CONNECTOR,
+                ]
+
+                result = await db_session.execute(
+                    select(SearchSourceConnector).filter(
+                        SearchSourceConnector.id == final_connector_id,
+                        SearchSourceConnector.search_space_id == search_space_id,
+                        SearchSourceConnector.user_id == user_id,
+                        SearchSourceConnector.connector_type.in_(_gmail_types),
+                    )
+                )
+                connector = result.scalars().first()
+                if not connector:
+                    return {
+                        "status": "error",
+                        "message": "Selected Gmail connector is invalid or has been disconnected.",
+                    }
+
+                logger.info(
+                    f"Trashing Gmail email: message_id='{final_message_id}', connector={final_connector_id}"
+                )
+
+                is_composio_gmail = (
+                    connector.connector_type
+                    == SearchSourceConnectorType.COMPOSIO_GMAIL_CONNECTOR
+                )
+                if is_composio_gmail:
+                    cca_id = connector.config.get("composio_connected_account_id")
+                    if not cca_id:
+                        return {
+                            "status": "error",
+                            "message": "Composio connected account ID not found for this Gmail connector.",
+                        }
+                else:
+                    from google.oauth2.credentials import Credentials
+
+                    from app.config import config
+                    from app.utils.oauth_security import TokenEncryption
+
+                    config_data = dict(connector.config)
+                    token_encrypted = config_data.get("_token_encrypted", False)
+                    if token_encrypted and config.SECRET_KEY:
+                        token_encryption = TokenEncryption(config.SECRET_KEY)
+                        if config_data.get("token"):
+                            config_data["token"] = token_encryption.decrypt_token(
+                                config_data["token"]
+                            )
+                        if config_data.get("refresh_token"):
+                            config_data["refresh_token"] = (
+                                token_encryption.decrypt_token(
+                                    config_data["refresh_token"]
+                                )
+                            )
+                        if config_data.get("client_secret"):
+                            config_data["client_secret"] = (
+                                token_encryption.decrypt_token(
+                                    config_data["client_secret"]
+                                )
+                            )
+
+                    exp = config_data.get("expiry", "")
+                    if exp:
+                        exp = exp.replace("Z", "")
+
+                    creds = Credentials(
+                        token=config_data.get("token"),
+                        refresh_token=config_data.get("refresh_token"),
+                        token_uri=config_data.get("token_uri"),
+                        client_id=config_data.get("client_id"),
+                        client_secret=config_data.get("client_secret"),
+                        scopes=config_data.get("scopes", []),
+                        expiry=datetime.fromisoformat(exp) if exp else None,
+                    )
+
+                try:
+                    if is_composio_gmail:
+                        from app.agents.new_chat.tools.gmail.composio_helpers import (
+                            execute_composio_gmail_tool,
+                        )
+
+                        _trashed, error = await execute_composio_gmail_tool(
+                            connector,
+                            user_id,
+                            "GMAIL_MOVE_TO_TRASH",
+                            {"user_id": "me", "message_id": final_message_id},
+                        )
+                        if error:
+                            raise RuntimeError(error)
+                    else:
+                        from googleapiclient.discovery import build
+
+                        gmail_service = build("gmail", "v1", credentials=creds)
+                        await asyncio.get_event_loop().run_in_executor(
+                            None,
+                            lambda: (
+                                gmail_service.users()
+                                .messages()
+                                .trash(userId="me", id=final_message_id)
+                                .execute()
+                            ),
+                        )
+                except Exception as api_err:
+                    from googleapiclient.errors import HttpError
+
+                    if isinstance(api_err, HttpError) and api_err.resp.status == 403:
+                        logger.warning(
+                            f"Insufficient permissions for connector {connector.id}: {api_err}"
+                        )
+                        try:
+                            from sqlalchemy.orm.attributes import flag_modified
+
+                            if not connector.config.get("auth_expired"):
+                                connector.config = {
+                                    **connector.config,
+                                    "auth_expired": True,
+                                }
+                                flag_modified(connector, "config")
+                                await db_session.commit()
+                        except Exception:
+                            logger.warning(
+                                "Failed to persist auth_expired for connector %s",
+                                connector.id,
+                                exc_info=True,
+                            )
+                        return {
+                            "status": "insufficient_permissions",
+                            "connector_id": connector.id,
+                            "message": "This Gmail account needs additional permissions. Please re-authenticate in connector settings.",
+                        }
+                    raise
+
+                logger.info(f"Gmail email trashed: message_id={final_message_id}")
+
+                trash_result: dict[str, Any] = {
+                    "status": "success",
+                    "message_id": final_message_id,
+                    "message": f"Successfully moved email '{email.get('subject', email_subject_or_id)}' to trash.",
+                }
+
+                deleted_from_kb = False
+                if final_delete_from_kb and document_id:
+                    try:
+                        from app.db import Document
+
+                        doc_result = await db_session.execute(
+                            select(Document).filter(Document.id == document_id)
+                        )
+                        document = doc_result.scalars().first()
+                        if document:
+                            await db_session.delete(document)
+                            await db_session.commit()
+                            deleted_from_kb = True
+                            logger.info(
+                                f"Deleted document {document_id} from knowledge base"
+                            )
+                        else:
+                            logger.warning(f"Document {document_id} not found in KB")
+                    except Exception as e:
+                        logger.error(f"Failed to delete document from KB: {e}")
+                        await db_session.rollback()
+                        trash_result["warning"] = (
+                            f"Email trashed, but failed to remove from knowledge base: {e!s}"
+                        )
+
+                trash_result["deleted_from_kb"] = deleted_from_kb
+                if deleted_from_kb:
+                    trash_result["message"] = (
+                        f"{trash_result.get('message', '')} (also removed from knowledge base)"
+                    )
+
+                return trash_result
 
         except Exception as e:
             from langgraph.errors import GraphInterrupt

surfsense_backend/app/agents/new_chat/tools/gmail/update_draft.py

@@ -9,6 +9,7 @@ from langchain_core.tools import tool
 from sqlalchemy.ext.asyncio import AsyncSession
 
 from app.agents.new_chat.tools.hitl import request_approval
+from app.db import async_session_maker
 from app.services.gmail import GmailToolMetadataService
 
 logger = logging.getLogger(__name__)
@@ -19,6 +20,23 @@ def create_update_gmail_draft_tool(
     search_space_id: int | None = None,
     user_id: str | None = None,
 ):
+    """
+    Factory function to create the update_gmail_draft tool.
+
+    The tool acquires its own short-lived ``AsyncSession`` per call via
+    :data:`async_session_maker` so the closure is safe to share across
+    HTTP requests by the compiled-agent cache. Capturing a per-request
+    session here would surface stale/closed sessions on cache hits.
+
+    Args:
+        db_session: Reserved for registry compatibility. Per-call sessions
+            are opened via :data:`async_session_maker` inside the tool body.
+
+    Returns:
+        Configured update_gmail_draft tool
+    """
+    del db_session  # per-call session — see docstring
+
     @tool
     async def update_gmail_draft(
         draft_subject_or_id: str,
@@ -76,324 +94,329 @@ def create_update_gmail_draft_tool(
             f"update_gmail_draft called: draft_subject_or_id='{draft_subject_or_id}'"
         )
 
-        if db_session is None or search_space_id is None or user_id is None:
+        if search_space_id is None or user_id is None:
             return {
                 "status": "error",
                 "message": "Gmail tool not properly configured. Please contact support.",
             }
 
         try:
-            metadata_service = GmailToolMetadataService(db_session)
-            context = await metadata_service.get_update_context(
-                search_space_id, user_id, draft_subject_or_id
-            )
-
-            if "error" in context:
-                error_msg = context["error"]
-                if "not found" in error_msg.lower():
-                    logger.warning(f"Draft not found: {error_msg}")
-                    return {"status": "not_found", "message": error_msg}
-                logger.error(f"Failed to fetch update context: {error_msg}")
-                return {"status": "error", "message": error_msg}
-
-            account = context.get("account", {})
-            if account.get("auth_expired"):
-                logger.warning(
-                    "Gmail account %s has expired authentication",
-                    account.get("id"),
-                )
-                return {
-                    "status": "auth_error",
-                    "message": "The Gmail account for this draft needs re-authentication. Please re-authenticate in your connector settings.",
-                    "connector_type": "gmail",
-                }
-
-            email = context["email"]
-            message_id = email["message_id"]
-            document_id = email.get("document_id")
-            connector_id_from_context = account["id"]
-            draft_id_from_context = context.get("draft_id")
-
-            original_subject = email.get("subject", draft_subject_or_id)
-            final_subject_default = subject if subject else original_subject
-            final_to_default = to if to else ""
-
-            logger.info(
-                f"Requesting approval for updating Gmail draft: '{original_subject}' "
-                f"(message_id={message_id}, draft_id={draft_id_from_context})"
-            )
-            result = request_approval(
-                action_type="gmail_draft_update",
-                tool_name="update_gmail_draft",
-                params={
-                    "message_id": message_id,
-                    "draft_id": draft_id_from_context,
-                    "to": final_to_default,
-                    "subject": final_subject_default,
-                    "body": body,
-                    "cc": cc,
-                    "bcc": bcc,
-                    "connector_id": connector_id_from_context,
-                },
-                context=context,
-            )
-
-            if result.rejected:
-                return {
-                    "status": "rejected",
-                    "message": "User declined. The draft was not updated. Do not ask again or suggest alternatives.",
-                }
-
-            final_to = result.params.get("to", final_to_default)
-            final_subject = result.params.get("subject", final_subject_default)
-            final_body = result.params.get("body", body)
-            final_cc = result.params.get("cc", cc)
-            final_bcc = result.params.get("bcc", bcc)
-            final_connector_id = result.params.get(
-                "connector_id", connector_id_from_context
-            )
-            final_draft_id = result.params.get("draft_id", draft_id_from_context)
-
-            if not final_connector_id:
-                return {
-                    "status": "error",
-                    "message": "No connector found for this draft.",
-                }
-
-            from sqlalchemy.future import select
-
-            from app.db import SearchSourceConnector, SearchSourceConnectorType
-
-            _gmail_types = [
-                SearchSourceConnectorType.GOOGLE_GMAIL_CONNECTOR,
-                SearchSourceConnectorType.COMPOSIO_GMAIL_CONNECTOR,
-            ]
-
-            result = await db_session.execute(
-                select(SearchSourceConnector).filter(
-                    SearchSourceConnector.id == final_connector_id,
-                    SearchSourceConnector.search_space_id == search_space_id,
-                    SearchSourceConnector.user_id == user_id,
-                    SearchSourceConnector.connector_type.in_(_gmail_types),
-                )
-            )
-            connector = result.scalars().first()
-            if not connector:
-                return {
-                    "status": "error",
-                    "message": "Selected Gmail connector is invalid or has been disconnected.",
-                }
-
-            logger.info(
-                f"Updating Gmail draft: subject='{final_subject}', connector={final_connector_id}"
-            )
-
-            is_composio_gmail = (
-                connector.connector_type
-                == SearchSourceConnectorType.COMPOSIO_GMAIL_CONNECTOR
-            )
-            if is_composio_gmail:
-                cca_id = connector.config.get("composio_connected_account_id")
-                if not cca_id:
-                    return {
-                        "status": "error",
-                        "message": "Composio connected account ID not found for this Gmail connector.",
-                    }
-            else:
-                from google.oauth2.credentials import Credentials
-
-                from app.config import config
-                from app.utils.oauth_security import TokenEncryption
-
-                config_data = dict(connector.config)
-                token_encrypted = config_data.get("_token_encrypted", False)
-                if token_encrypted and config.SECRET_KEY:
-                    token_encryption = TokenEncryption(config.SECRET_KEY)
-                    if config_data.get("token"):
-                        config_data["token"] = token_encryption.decrypt_token(
-                            config_data["token"]
-                        )
-                    if config_data.get("refresh_token"):
-                        config_data["refresh_token"] = token_encryption.decrypt_token(
-                            config_data["refresh_token"]
-                        )
-                    if config_data.get("client_secret"):
-                        config_data["client_secret"] = token_encryption.decrypt_token(
-                            config_data["client_secret"]
-                        )
-
-                exp = config_data.get("expiry", "")
-                if exp:
-                    exp = exp.replace("Z", "")
-
-                creds = Credentials(
-                    token=config_data.get("token"),
-                    refresh_token=config_data.get("refresh_token"),
-                    token_uri=config_data.get("token_uri"),
-                    client_id=config_data.get("client_id"),
-                    client_secret=config_data.get("client_secret"),
-                    scopes=config_data.get("scopes", []),
-                    expiry=datetime.fromisoformat(exp) if exp else None,
+            async with async_session_maker() as db_session:
+                metadata_service = GmailToolMetadataService(db_session)
+                context = await metadata_service.get_update_context(
+                    search_space_id, user_id, draft_subject_or_id
                 )
 
-            # Resolve draft_id if not already available
-            if not final_draft_id:
-                logger.info(
-                    f"draft_id not in metadata, looking up via drafts.list for message_id={message_id}"
-                )
-                if is_composio_gmail:
-                    final_draft_id = await _find_composio_draft_id_by_message(
-                        connector, user_id, message_id
-                    )
-                else:
-                    from googleapiclient.discovery import build
+                if "error" in context:
+                    error_msg = context["error"]
+                    if "not found" in error_msg.lower():
+                        logger.warning(f"Draft not found: {error_msg}")
+                        return {"status": "not_found", "message": error_msg}
+                    logger.error(f"Failed to fetch update context: {error_msg}")
+                    return {"status": "error", "message": error_msg}
 
-                    gmail_service = build("gmail", "v1", credentials=creds)
-                    final_draft_id = await _find_draft_id_by_message(
-                        gmail_service, message_id
-                    )
-
-            if not final_draft_id:
-                return {
-                    "status": "error",
-                    "message": (
-                        "Could not find this draft in Gmail. "
-                        "It may have already been sent or deleted."
-                    ),
-                }
-
-            message = MIMEText(final_body)
-            if final_to:
-                message["to"] = final_to
-            message["subject"] = final_subject
-            if final_cc:
-                message["cc"] = final_cc
-            if final_bcc:
-                message["bcc"] = final_bcc
-            raw = base64.urlsafe_b64encode(message.as_bytes()).decode()
-
-            try:
-                if is_composio_gmail:
-                    from app.agents.new_chat.tools.gmail.composio_helpers import (
-                        execute_composio_gmail_tool,
-                        split_recipients,
-                    )
-
-                    updated, error = await execute_composio_gmail_tool(
-                        connector,
-                        user_id,
-                        "GMAIL_UPDATE_DRAFT",
-                        {
-                            "user_id": "me",
-                            "draft_id": final_draft_id,
-                            "recipient_email": final_to,
-                            "subject": final_subject,
-                            "body": final_body,
-                            "cc": split_recipients(final_cc),
-                            "bcc": split_recipients(final_bcc),
-                            "is_html": False,
-                        },
-                    )
-                    if error:
-                        raise RuntimeError(error)
-                    if not isinstance(updated, dict):
-                        updated = {}
-                else:
-                    from googleapiclient.discovery import build
-
-                    gmail_service = build("gmail", "v1", credentials=creds)
-                    updated = await asyncio.get_event_loop().run_in_executor(
-                        None,
-                        lambda: (
-                            gmail_service.users()
-                            .drafts()
-                            .update(
-                                userId="me",
-                                id=final_draft_id,
-                                body={"message": {"raw": raw}},
-                            )
-                            .execute()
-                        ),
-                    )
-            except Exception as api_err:
-                from googleapiclient.errors import HttpError
-
-                if isinstance(api_err, HttpError) and api_err.resp.status == 403:
+                account = context.get("account", {})
+                if account.get("auth_expired"):
                     logger.warning(
-                        f"Insufficient permissions for connector {connector.id}: {api_err}"
+                        "Gmail account %s has expired authentication",
+                        account.get("id"),
                     )
-                    try:
-                        from sqlalchemy.orm.attributes import flag_modified
-
-                        if not connector.config.get("auth_expired"):
-                            connector.config = {
-                                **connector.config,
-                                "auth_expired": True,
-                            }
-                            flag_modified(connector, "config")
-                            await db_session.commit()
-                    except Exception:
-                        logger.warning(
-                            "Failed to persist auth_expired for connector %s",
-                            connector.id,
-                            exc_info=True,
-                        )
                     return {
-                        "status": "insufficient_permissions",
-                        "connector_id": connector.id,
-                        "message": "This Gmail account needs additional permissions. Please re-authenticate in connector settings.",
+                        "status": "auth_error",
+                        "message": "The Gmail account for this draft needs re-authentication. Please re-authenticate in your connector settings.",
+                        "connector_type": "gmail",
                     }
-                if isinstance(api_err, HttpError) and api_err.resp.status == 404:
+
+                email = context["email"]
+                message_id = email["message_id"]
+                document_id = email.get("document_id")
+                connector_id_from_context = account["id"]
+                draft_id_from_context = context.get("draft_id")
+
+                original_subject = email.get("subject", draft_subject_or_id)
+                final_subject_default = subject if subject else original_subject
+                final_to_default = to if to else ""
+
+                logger.info(
+                    f"Requesting approval for updating Gmail draft: '{original_subject}' "
+                    f"(message_id={message_id}, draft_id={draft_id_from_context})"
+                )
+                result = request_approval(
+                    action_type="gmail_draft_update",
+                    tool_name="update_gmail_draft",
+                    params={
+                        "message_id": message_id,
+                        "draft_id": draft_id_from_context,
+                        "to": final_to_default,
+                        "subject": final_subject_default,
+                        "body": body,
+                        "cc": cc,
+                        "bcc": bcc,
+                        "connector_id": connector_id_from_context,
+                    },
+                    context=context,
+                )
+
+                if result.rejected:
+                    return {
+                        "status": "rejected",
+                        "message": "User declined. The draft was not updated. Do not ask again or suggest alternatives.",
+                    }
+
+                final_to = result.params.get("to", final_to_default)
+                final_subject = result.params.get("subject", final_subject_default)
+                final_body = result.params.get("body", body)
+                final_cc = result.params.get("cc", cc)
+                final_bcc = result.params.get("bcc", bcc)
+                final_connector_id = result.params.get(
+                    "connector_id", connector_id_from_context
+                )
+                final_draft_id = result.params.get("draft_id", draft_id_from_context)
+
+                if not final_connector_id:
                     return {
                         "status": "error",
-                        "message": "Draft no longer exists in Gmail. It may have been sent or deleted.",
+                        "message": "No connector found for this draft.",
                     }
-                raise
 
-            logger.info(f"Gmail draft updated: id={updated.get('id')}")
+                from sqlalchemy.future import select
 
-            kb_message_suffix = ""
-            if document_id:
-                try:
-                    from sqlalchemy.future import select as sa_select
-                    from sqlalchemy.orm.attributes import flag_modified
+                from app.db import SearchSourceConnector, SearchSourceConnectorType
 
-                    from app.db import Document
+                _gmail_types = [
+                    SearchSourceConnectorType.GOOGLE_GMAIL_CONNECTOR,
+                    SearchSourceConnectorType.COMPOSIO_GMAIL_CONNECTOR,
+                ]
 
-                    doc_result = await db_session.execute(
-                        sa_select(Document).filter(Document.id == document_id)
+                result = await db_session.execute(
+                    select(SearchSourceConnector).filter(
+                        SearchSourceConnector.id == final_connector_id,
+                        SearchSourceConnector.search_space_id == search_space_id,
+                        SearchSourceConnector.user_id == user_id,
+                        SearchSourceConnector.connector_type.in_(_gmail_types),
                     )
-                    document = doc_result.scalars().first()
-                    if document:
-                        document.source_markdown = final_body
-                        document.title = final_subject
-                        meta = dict(document.document_metadata or {})
-                        meta["subject"] = final_subject
-                        meta["draft_id"] = updated.get("id", final_draft_id)
-                        updated_msg = updated.get("message", {})
-                        if updated_msg.get("id"):
-                            meta["message_id"] = updated_msg["id"]
-                        document.document_metadata = meta
-                        flag_modified(document, "document_metadata")
-                        await db_session.commit()
-                        kb_message_suffix = (
-                            " Your knowledge base has also been updated."
-                        )
-                        logger.info(
-                            f"KB document {document_id} updated for draft {final_draft_id}"
+                )
+                connector = result.scalars().first()
+                if not connector:
+                    return {
+                        "status": "error",
+                        "message": "Selected Gmail connector is invalid or has been disconnected.",
+                    }
+
+                logger.info(
+                    f"Updating Gmail draft: subject='{final_subject}', connector={final_connector_id}"
+                )
+
+                is_composio_gmail = (
+                    connector.connector_type
+                    == SearchSourceConnectorType.COMPOSIO_GMAIL_CONNECTOR
+                )
+                if is_composio_gmail:
+                    cca_id = connector.config.get("composio_connected_account_id")
+                    if not cca_id:
+                        return {
+                            "status": "error",
+                            "message": "Composio connected account ID not found for this Gmail connector.",
+                        }
+                else:
+                    from google.oauth2.credentials import Credentials
+
+                    from app.config import config
+                    from app.utils.oauth_security import TokenEncryption
+
+                    config_data = dict(connector.config)
+                    token_encrypted = config_data.get("_token_encrypted", False)
+                    if token_encrypted and config.SECRET_KEY:
+                        token_encryption = TokenEncryption(config.SECRET_KEY)
+                        if config_data.get("token"):
+                            config_data["token"] = token_encryption.decrypt_token(
+                                config_data["token"]
+                            )
+                        if config_data.get("refresh_token"):
+                            config_data["refresh_token"] = (
+                                token_encryption.decrypt_token(
+                                    config_data["refresh_token"]
+                                )
+                            )
+                        if config_data.get("client_secret"):
+                            config_data["client_secret"] = (
+                                token_encryption.decrypt_token(
+                                    config_data["client_secret"]
+                                )
+                            )
+
+                    exp = config_data.get("expiry", "")
+                    if exp:
+                        exp = exp.replace("Z", "")
+
+                    creds = Credentials(
+                        token=config_data.get("token"),
+                        refresh_token=config_data.get("refresh_token"),
+                        token_uri=config_data.get("token_uri"),
+                        client_id=config_data.get("client_id"),
+                        client_secret=config_data.get("client_secret"),
+                        scopes=config_data.get("scopes", []),
+                        expiry=datetime.fromisoformat(exp) if exp else None,
+                    )
+
+                # Resolve draft_id if not already available
+                if not final_draft_id:
+                    logger.info(
+                        f"draft_id not in metadata, looking up via drafts.list for message_id={message_id}"
+                    )
+                    if is_composio_gmail:
+                        final_draft_id = await _find_composio_draft_id_by_message(
+                            connector, user_id, message_id
                         )
                     else:
-                        kb_message_suffix = " This draft will be fully updated in your knowledge base in the next scheduled sync."
-                except Exception as kb_err:
-                    logger.warning(f"KB update after draft edit failed: {kb_err}")
-                    await db_session.rollback()
-                    kb_message_suffix = " This draft will be fully updated in your knowledge base in the next scheduled sync."
+                        from googleapiclient.discovery import build
 
-            return {
-                "status": "success",
-                "draft_id": updated.get("id"),
-                "message": f"Successfully updated Gmail draft with subject '{final_subject}'.{kb_message_suffix}",
-            }
+                        gmail_service = build("gmail", "v1", credentials=creds)
+                        final_draft_id = await _find_draft_id_by_message(
+                            gmail_service, message_id
+                        )
+
+                if not final_draft_id:
+                    return {
+                        "status": "error",
+                        "message": (
+                            "Could not find this draft in Gmail. "
+                            "It may have already been sent or deleted."
+                        ),
+                    }
+
+                message = MIMEText(final_body)
+                if final_to:
+                    message["to"] = final_to
+                message["subject"] = final_subject
+                if final_cc:
+                    message["cc"] = final_cc
+                if final_bcc:
+                    message["bcc"] = final_bcc
+                raw = base64.urlsafe_b64encode(message.as_bytes()).decode()
+
+                try:
+                    if is_composio_gmail:
+                        from app.agents.new_chat.tools.gmail.composio_helpers import (
+                            execute_composio_gmail_tool,
+                            split_recipients,
+                        )
+
+                        updated, error = await execute_composio_gmail_tool(
+                            connector,
+                            user_id,
+                            "GMAIL_UPDATE_DRAFT",
+                            {
+                                "user_id": "me",
+                                "draft_id": final_draft_id,
+                                "recipient_email": final_to,
+                                "subject": final_subject,
+                                "body": final_body,
+                                "cc": split_recipients(final_cc),
+                                "bcc": split_recipients(final_bcc),
+                                "is_html": False,
+                            },
+                        )
+                        if error:
+                            raise RuntimeError(error)
+                        if not isinstance(updated, dict):
+                            updated = {}
+                    else:
+                        from googleapiclient.discovery import build
+
+                        gmail_service = build("gmail", "v1", credentials=creds)
+                        updated = await asyncio.get_event_loop().run_in_executor(
+                            None,
+                            lambda: (
+                                gmail_service.users()
+                                .drafts()
+                                .update(
+                                    userId="me",
+                                    id=final_draft_id,
+                                    body={"message": {"raw": raw}},
+                                )
+                                .execute()
+                            ),
+                        )
+                except Exception as api_err:
+                    from googleapiclient.errors import HttpError
+
+                    if isinstance(api_err, HttpError) and api_err.resp.status == 403:
+                        logger.warning(
+                            f"Insufficient permissions for connector {connector.id}: {api_err}"
+                        )
+                        try:
+                            from sqlalchemy.orm.attributes import flag_modified
+
+                            if not connector.config.get("auth_expired"):
+                                connector.config = {
+                                    **connector.config,
+                                    "auth_expired": True,
+                                }
+                                flag_modified(connector, "config")
+                                await db_session.commit()
+                        except Exception:
+                            logger.warning(
+                                "Failed to persist auth_expired for connector %s",
+                                connector.id,
+                                exc_info=True,
+                            )
+                        return {
+                            "status": "insufficient_permissions",
+                            "connector_id": connector.id,
+                            "message": "This Gmail account needs additional permissions. Please re-authenticate in connector settings.",
+                        }
+                    if isinstance(api_err, HttpError) and api_err.resp.status == 404:
+                        return {
+                            "status": "error",
+                            "message": "Draft no longer exists in Gmail. It may have been sent or deleted.",
+                        }
+                    raise
+
+                logger.info(f"Gmail draft updated: id={updated.get('id')}")
+
+                kb_message_suffix = ""
+                if document_id:
+                    try:
+                        from sqlalchemy.future import select as sa_select
+                        from sqlalchemy.orm.attributes import flag_modified
+
+                        from app.db import Document
+
+                        doc_result = await db_session.execute(
+                            sa_select(Document).filter(Document.id == document_id)
+                        )
+                        document = doc_result.scalars().first()
+                        if document:
+                            document.source_markdown = final_body
+                            document.title = final_subject
+                            meta = dict(document.document_metadata or {})
+                            meta["subject"] = final_subject
+                            meta["draft_id"] = updated.get("id", final_draft_id)
+                            updated_msg = updated.get("message", {})
+                            if updated_msg.get("id"):
+                                meta["message_id"] = updated_msg["id"]
+                            document.document_metadata = meta
+                            flag_modified(document, "document_metadata")
+                            await db_session.commit()
+                            kb_message_suffix = (
+                                " Your knowledge base has also been updated."
+                            )
+                            logger.info(
+                                f"KB document {document_id} updated for draft {final_draft_id}"
+                            )
+                        else:
+                            kb_message_suffix = " This draft will be fully updated in your knowledge base in the next scheduled sync."
+                    except Exception as kb_err:
+                        logger.warning(f"KB update after draft edit failed: {kb_err}")
+                        await db_session.rollback()
+                        kb_message_suffix = " This draft will be fully updated in your knowledge base in the next scheduled sync."
+
+                return {
+                    "status": "success",
+                    "draft_id": updated.get("id"),
+                    "message": f"Successfully updated Gmail draft with subject '{final_subject}'.{kb_message_suffix}",
+                }
 
         except Exception as e:
             from langgraph.errors import GraphInterrupt

surfsense_backend/app/agents/new_chat/tools/google_calendar/create_event.py

@@ -9,6 +9,7 @@ from langchain_core.tools import tool
 from sqlalchemy.ext.asyncio import AsyncSession
 
 from app.agents.new_chat.tools.hitl import request_approval
+from app.db import async_session_maker
 from app.services.google_calendar import GoogleCalendarToolMetadataService
 
 logger = logging.getLogger(__name__)
@@ -19,6 +20,23 @@ def create_create_calendar_event_tool(
     search_space_id: int | None = None,
     user_id: str | None = None,
 ):
+    """
+    Factory function to create the create_calendar_event tool.
+
+    The tool acquires its own short-lived ``AsyncSession`` per call via
+    :data:`async_session_maker` so the closure is safe to share across
+    HTTP requests by the compiled-agent cache. Capturing a per-request
+    session here would surface stale/closed sessions on cache hits.
+
+    Args:
+        db_session: Reserved for registry compatibility. Per-call sessions
+            are opened via :data:`async_session_maker` inside the tool body.
+
+    Returns:
+        Configured create_calendar_event tool
+    """
+    del db_session  # per-call session — see docstring
+
     @tool
     async def create_calendar_event(
         summary: str,
@@ -60,284 +78,294 @@ def create_create_calendar_event_tool(
             f"create_calendar_event called: summary='{summary}', start='{start_datetime}', end='{end_datetime}'"
         )
 
-        if db_session is None or search_space_id is None or user_id is None:
+        if search_space_id is None or user_id is None:
             return {
                 "status": "error",
                 "message": "Google Calendar tool not properly configured. Please contact support.",
             }
 
         try:
-            metadata_service = GoogleCalendarToolMetadataService(db_session)
-            context = await metadata_service.get_creation_context(
-                search_space_id, user_id
-            )
-
-            if "error" in context:
-                logger.error(f"Failed to fetch creation context: {context['error']}")
-                return {"status": "error", "message": context["error"]}
-
-            accounts = context.get("accounts", [])
-            if accounts and all(a.get("auth_expired") for a in accounts):
-                logger.warning(
-                    "All Google Calendar accounts have expired authentication"
+            async with async_session_maker() as db_session:
+                metadata_service = GoogleCalendarToolMetadataService(db_session)
+                context = await metadata_service.get_creation_context(
+                    search_space_id, user_id
                 )
-                return {
-                    "status": "auth_error",
-                    "message": "All connected Google Calendar accounts need re-authentication. Please re-authenticate in your connector settings.",
-                    "connector_type": "google_calendar",
-                }
 
-            logger.info(
-                f"Requesting approval for creating calendar event: summary='{summary}'"
-            )
-            result = request_approval(
-                action_type="google_calendar_event_creation",
-                tool_name="create_calendar_event",
-                params={
-                    "summary": summary,
-                    "start_datetime": start_datetime,
-                    "end_datetime": end_datetime,
-                    "description": description,
-                    "location": location,
-                    "attendees": attendees,
-                    "timezone": context.get("timezone"),
-                    "connector_id": None,
-                },
-                context=context,
-            )
-
-            if result.rejected:
-                return {
-                    "status": "rejected",
-                    "message": "User declined. The event was not created. Do not ask again or suggest alternatives.",
-                }
-
-            final_summary = result.params.get("summary", summary)
-            final_start_datetime = result.params.get("start_datetime", start_datetime)
-            final_end_datetime = result.params.get("end_datetime", end_datetime)
-            final_description = result.params.get("description", description)
-            final_location = result.params.get("location", location)
-            final_attendees = result.params.get("attendees", attendees)
-            final_connector_id = result.params.get("connector_id")
-
-            if not final_summary or not final_summary.strip():
-                return {"status": "error", "message": "Event summary cannot be empty."}
-
-            from sqlalchemy.future import select
-
-            from app.db import SearchSourceConnector, SearchSourceConnectorType
-
-            _calendar_types = [
-                SearchSourceConnectorType.GOOGLE_CALENDAR_CONNECTOR,
-                SearchSourceConnectorType.COMPOSIO_GOOGLE_CALENDAR_CONNECTOR,
-            ]
-
-            if final_connector_id is not None:
-                result = await db_session.execute(
-                    select(SearchSourceConnector).filter(
-                        SearchSourceConnector.id == final_connector_id,
-                        SearchSourceConnector.search_space_id == search_space_id,
-                        SearchSourceConnector.user_id == user_id,
-                        SearchSourceConnector.connector_type.in_(_calendar_types),
+                if "error" in context:
+                    logger.error(
+                        f"Failed to fetch creation context: {context['error']}"
                     )
-                )
-                connector = result.scalars().first()
-                if not connector:
-                    return {
-                        "status": "error",
-                        "message": "Selected Google Calendar connector is invalid or has been disconnected.",
-                    }
-                actual_connector_id = connector.id
-            else:
-                result = await db_session.execute(
-                    select(SearchSourceConnector).filter(
-                        SearchSourceConnector.search_space_id == search_space_id,
-                        SearchSourceConnector.user_id == user_id,
-                        SearchSourceConnector.connector_type.in_(_calendar_types),
+                    return {"status": "error", "message": context["error"]}
+
+                accounts = context.get("accounts", [])
+                if accounts and all(a.get("auth_expired") for a in accounts):
+                    logger.warning(
+                        "All Google Calendar accounts have expired authentication"
                     )
+                    return {
+                        "status": "auth_error",
+                        "message": "All connected Google Calendar accounts need re-authentication. Please re-authenticate in your connector settings.",
+                        "connector_type": "google_calendar",
+                    }
+
+                logger.info(
+                    f"Requesting approval for creating calendar event: summary='{summary}'"
                 )
-                connector = result.scalars().first()
-                if not connector:
-                    return {
-                        "status": "error",
-                        "message": "No Google Calendar connector found. Please connect Google Calendar in your workspace settings.",
-                    }
-                actual_connector_id = connector.id
-
-            logger.info(
-                f"Creating calendar event: summary='{final_summary}', connector={actual_connector_id}"
-            )
-
-            is_composio_calendar = (
-                connector.connector_type
-                == SearchSourceConnectorType.COMPOSIO_GOOGLE_CALENDAR_CONNECTOR
-            )
-            if is_composio_calendar:
-                cca_id = connector.config.get("composio_connected_account_id")
-                if not cca_id:
-                    return {
-                        "status": "error",
-                        "message": "Composio connected account ID not found for this connector.",
-                    }
-            else:
-                config_data = dict(connector.config)
-
-                from app.config import config as app_config
-                from app.utils.oauth_security import TokenEncryption
-
-                token_encrypted = config_data.get("_token_encrypted", False)
-                if token_encrypted and app_config.SECRET_KEY:
-                    token_encryption = TokenEncryption(app_config.SECRET_KEY)
-                    for key in ("token", "refresh_token", "client_secret"):
-                        if config_data.get(key):
-                            config_data[key] = token_encryption.decrypt_token(
-                                config_data[key]
-                            )
-
-                exp = config_data.get("expiry", "")
-                if exp:
-                    exp = exp.replace("Z", "")
-
-                creds = Credentials(
-                    token=config_data.get("token"),
-                    refresh_token=config_data.get("refresh_token"),
-                    token_uri=config_data.get("token_uri"),
-                    client_id=config_data.get("client_id"),
-                    client_secret=config_data.get("client_secret"),
-                    scopes=config_data.get("scopes", []),
-                    expiry=datetime.fromisoformat(exp) if exp else None,
+                result = request_approval(
+                    action_type="google_calendar_event_creation",
+                    tool_name="create_calendar_event",
+                    params={
+                        "summary": summary,
+                        "start_datetime": start_datetime,
+                        "end_datetime": end_datetime,
+                        "description": description,
+                        "location": location,
+                        "attendees": attendees,
+                        "timezone": context.get("timezone"),
+                        "connector_id": None,
+                    },
+                    context=context,
                 )
 
-            tz = context.get("timezone", "UTC")
-            event_body: dict[str, Any] = {
-                "summary": final_summary,
-                "start": {"dateTime": final_start_datetime, "timeZone": tz},
-                "end": {"dateTime": final_end_datetime, "timeZone": tz},
-            }
-            if final_description:
-                event_body["description"] = final_description
-            if final_location:
-                event_body["location"] = final_location
-            if final_attendees:
-                event_body["attendees"] = [
-                    {"email": e.strip()} for e in final_attendees if e.strip()
+                if result.rejected:
+                    return {
+                        "status": "rejected",
+                        "message": "User declined. The event was not created. Do not ask again or suggest alternatives.",
+                    }
+
+                final_summary = result.params.get("summary", summary)
+                final_start_datetime = result.params.get(
+                    "start_datetime", start_datetime
+                )
+                final_end_datetime = result.params.get("end_datetime", end_datetime)
+                final_description = result.params.get("description", description)
+                final_location = result.params.get("location", location)
+                final_attendees = result.params.get("attendees", attendees)
+                final_connector_id = result.params.get("connector_id")
+
+                if not final_summary or not final_summary.strip():
+                    return {
+                        "status": "error",
+                        "message": "Event summary cannot be empty.",
+                    }
+
+                from sqlalchemy.future import select
+
+                from app.db import SearchSourceConnector, SearchSourceConnectorType
+
+                _calendar_types = [
+                    SearchSourceConnectorType.GOOGLE_CALENDAR_CONNECTOR,
+                    SearchSourceConnectorType.COMPOSIO_GOOGLE_CALENDAR_CONNECTOR,
                 ]
 
-            try:
-                if is_composio_calendar:
-                    from app.services.composio_service import ComposioService
-
-                    composio_params = {
-                        "calendar_id": "primary",
-                        "summary": final_summary,
-                        "start_datetime": final_start_datetime,
-                        "end_datetime": final_end_datetime,
-                        "timezone": tz,
-                        "attendees": final_attendees or [],
-                    }
-                    if final_description:
-                        composio_params["description"] = final_description
-                    if final_location:
-                        composio_params["location"] = final_location
-
-                    composio_result = await ComposioService().execute_tool(
-                        connected_account_id=cca_id,
-                        tool_name="GOOGLECALENDAR_CREATE_EVENT",
-                        params=composio_params,
-                        entity_id=f"surfsense_{user_id}",
-                    )
-                    if not composio_result.get("success"):
-                        raise RuntimeError(
-                            composio_result.get(
-                                "error", "Unknown Composio Calendar error"
-                            )
+                if final_connector_id is not None:
+                    result = await db_session.execute(
+                        select(SearchSourceConnector).filter(
+                            SearchSourceConnector.id == final_connector_id,
+                            SearchSourceConnector.search_space_id == search_space_id,
+                            SearchSourceConnector.user_id == user_id,
+                            SearchSourceConnector.connector_type.in_(_calendar_types),
                         )
-                    created = composio_result.get("data", {})
-                    if isinstance(created, dict):
-                        created = created.get("data", created)
-                        if isinstance(created, dict):
-                            created = created.get("response_data", created)
+                    )
+                    connector = result.scalars().first()
+                    if not connector:
+                        return {
+                            "status": "error",
+                            "message": "Selected Google Calendar connector is invalid or has been disconnected.",
+                        }
+                    actual_connector_id = connector.id
                 else:
-                    service = await asyncio.get_event_loop().run_in_executor(
-                        None, lambda: build("calendar", "v3", credentials=creds)
-                    )
-                    created = await asyncio.get_event_loop().run_in_executor(
-                        None,
-                        lambda: (
-                            service.events()
-                            .insert(calendarId="primary", body=event_body)
-                            .execute()
-                        ),
-                    )
-            except Exception as api_err:
-                from googleapiclient.errors import HttpError
-
-                if isinstance(api_err, HttpError) and api_err.resp.status == 403:
-                    logger.warning(
-                        f"Insufficient permissions for connector {actual_connector_id}: {api_err}"
-                    )
-                    try:
-                        from sqlalchemy.orm.attributes import flag_modified
-
-                        _res = await db_session.execute(
-                            select(SearchSourceConnector).where(
-                                SearchSourceConnector.id == actual_connector_id
-                            )
+                    result = await db_session.execute(
+                        select(SearchSourceConnector).filter(
+                            SearchSourceConnector.search_space_id == search_space_id,
+                            SearchSourceConnector.user_id == user_id,
+                            SearchSourceConnector.connector_type.in_(_calendar_types),
                         )
-                        _conn = _res.scalar_one_or_none()
-                        if _conn and not _conn.config.get("auth_expired"):
-                            _conn.config = {**_conn.config, "auth_expired": True}
-                            flag_modified(_conn, "config")
-                            await db_session.commit()
-                    except Exception:
-                        logger.warning(
-                            "Failed to persist auth_expired for connector %s",
-                            actual_connector_id,
-                            exc_info=True,
-                        )
-                    return {
-                        "status": "insufficient_permissions",
-                        "connector_id": actual_connector_id,
-                        "message": "This Google Calendar account needs additional permissions. Please re-authenticate in connector settings.",
-                    }
-                raise
+                    )
+                    connector = result.scalars().first()
+                    if not connector:
+                        return {
+                            "status": "error",
+                            "message": "No Google Calendar connector found. Please connect Google Calendar in your workspace settings.",
+                        }
+                    actual_connector_id = connector.id
 
-            logger.info(
-                f"Calendar event created: id={created.get('id')}, summary={created.get('summary')}"
-            )
-
-            kb_message_suffix = ""
-            try:
-                from app.services.google_calendar import GoogleCalendarKBSyncService
-
-                kb_service = GoogleCalendarKBSyncService(db_session)
-                kb_result = await kb_service.sync_after_create(
-                    event_id=created.get("id"),
-                    event_summary=final_summary,
-                    calendar_id="primary",
-                    start_time=final_start_datetime,
-                    end_time=final_end_datetime,
-                    location=final_location,
-                    html_link=created.get("htmlLink"),
-                    description=final_description,
-                    connector_id=actual_connector_id,
-                    search_space_id=search_space_id,
-                    user_id=user_id,
+                logger.info(
+                    f"Creating calendar event: summary='{final_summary}', connector={actual_connector_id}"
                 )
-                if kb_result["status"] == "success":
-                    kb_message_suffix = " Your knowledge base has also been updated."
-                else:
-                    kb_message_suffix = " This event will be added to your knowledge base in the next scheduled sync."
-            except Exception as kb_err:
-                logger.warning(f"KB sync after create failed: {kb_err}")
-                kb_message_suffix = " This event will be added to your knowledge base in the next scheduled sync."
 
-            return {
-                "status": "success",
-                "event_id": created.get("id"),
-                "html_link": created.get("htmlLink"),
-                "message": f"Successfully created '{final_summary}' on Google Calendar.{kb_message_suffix}",
-            }
+                is_composio_calendar = (
+                    connector.connector_type
+                    == SearchSourceConnectorType.COMPOSIO_GOOGLE_CALENDAR_CONNECTOR
+                )
+                if is_composio_calendar:
+                    cca_id = connector.config.get("composio_connected_account_id")
+                    if not cca_id:
+                        return {
+                            "status": "error",
+                            "message": "Composio connected account ID not found for this connector.",
+                        }
+                else:
+                    config_data = dict(connector.config)
+
+                    from app.config import config as app_config
+                    from app.utils.oauth_security import TokenEncryption
+
+                    token_encrypted = config_data.get("_token_encrypted", False)
+                    if token_encrypted and app_config.SECRET_KEY:
+                        token_encryption = TokenEncryption(app_config.SECRET_KEY)
+                        for key in ("token", "refresh_token", "client_secret"):
+                            if config_data.get(key):
+                                config_data[key] = token_encryption.decrypt_token(
+                                    config_data[key]
+                                )
+
+                    exp = config_data.get("expiry", "")
+                    if exp:
+                        exp = exp.replace("Z", "")
+
+                    creds = Credentials(
+                        token=config_data.get("token"),
+                        refresh_token=config_data.get("refresh_token"),
+                        token_uri=config_data.get("token_uri"),
+                        client_id=config_data.get("client_id"),
+                        client_secret=config_data.get("client_secret"),
+                        scopes=config_data.get("scopes", []),
+                        expiry=datetime.fromisoformat(exp) if exp else None,
+                    )
+
+                tz = context.get("timezone", "UTC")
+                event_body: dict[str, Any] = {
+                    "summary": final_summary,
+                    "start": {"dateTime": final_start_datetime, "timeZone": tz},
+                    "end": {"dateTime": final_end_datetime, "timeZone": tz},
+                }
+                if final_description:
+                    event_body["description"] = final_description
+                if final_location:
+                    event_body["location"] = final_location
+                if final_attendees:
+                    event_body["attendees"] = [
+                        {"email": e.strip()} for e in final_attendees if e.strip()
+                    ]
+
+                try:
+                    if is_composio_calendar:
+                        from app.services.composio_service import ComposioService
+
+                        composio_params = {
+                            "calendar_id": "primary",
+                            "summary": final_summary,
+                            "start_datetime": final_start_datetime,
+                            "end_datetime": final_end_datetime,
+                            "timezone": tz,
+                            "attendees": final_attendees or [],
+                        }
+                        if final_description:
+                            composio_params["description"] = final_description
+                        if final_location:
+                            composio_params["location"] = final_location
+
+                        composio_result = await ComposioService().execute_tool(
+                            connected_account_id=cca_id,
+                            tool_name="GOOGLECALENDAR_CREATE_EVENT",
+                            params=composio_params,
+                            entity_id=f"surfsense_{user_id}",
+                        )
+                        if not composio_result.get("success"):
+                            raise RuntimeError(
+                                composio_result.get(
+                                    "error", "Unknown Composio Calendar error"
+                                )
+                            )
+                        created = composio_result.get("data", {})
+                        if isinstance(created, dict):
+                            created = created.get("data", created)
+                            if isinstance(created, dict):
+                                created = created.get("response_data", created)
+                    else:
+                        service = await asyncio.get_event_loop().run_in_executor(
+                            None, lambda: build("calendar", "v3", credentials=creds)
+                        )
+                        created = await asyncio.get_event_loop().run_in_executor(
+                            None,
+                            lambda: (
+                                service.events()
+                                .insert(calendarId="primary", body=event_body)
+                                .execute()
+                            ),
+                        )
+                except Exception as api_err:
+                    from googleapiclient.errors import HttpError
+
+                    if isinstance(api_err, HttpError) and api_err.resp.status == 403:
+                        logger.warning(
+                            f"Insufficient permissions for connector {actual_connector_id}: {api_err}"
+                        )
+                        try:
+                            from sqlalchemy.orm.attributes import flag_modified
+
+                            _res = await db_session.execute(
+                                select(SearchSourceConnector).where(
+                                    SearchSourceConnector.id == actual_connector_id
+                                )
+                            )
+                            _conn = _res.scalar_one_or_none()
+                            if _conn and not _conn.config.get("auth_expired"):
+                                _conn.config = {**_conn.config, "auth_expired": True}
+                                flag_modified(_conn, "config")
+                                await db_session.commit()
+                        except Exception:
+                            logger.warning(
+                                "Failed to persist auth_expired for connector %s",
+                                actual_connector_id,
+                                exc_info=True,
+                            )
+                        return {
+                            "status": "insufficient_permissions",
+                            "connector_id": actual_connector_id,
+                            "message": "This Google Calendar account needs additional permissions. Please re-authenticate in connector settings.",
+                        }
+                    raise
+
+                logger.info(
+                    f"Calendar event created: id={created.get('id')}, summary={created.get('summary')}"
+                )
+
+                kb_message_suffix = ""
+                try:
+                    from app.services.google_calendar import GoogleCalendarKBSyncService
+
+                    kb_service = GoogleCalendarKBSyncService(db_session)
+                    kb_result = await kb_service.sync_after_create(
+                        event_id=created.get("id"),
+                        event_summary=final_summary,
+                        calendar_id="primary",
+                        start_time=final_start_datetime,
+                        end_time=final_end_datetime,
+                        location=final_location,
+                        html_link=created.get("htmlLink"),
+                        description=final_description,
+                        connector_id=actual_connector_id,
+                        search_space_id=search_space_id,
+                        user_id=user_id,
+                    )
+                    if kb_result["status"] == "success":
+                        kb_message_suffix = (
+                            " Your knowledge base has also been updated."
+                        )
+                    else:
+                        kb_message_suffix = " This event will be added to your knowledge base in the next scheduled sync."
+                except Exception as kb_err:
+                    logger.warning(f"KB sync after create failed: {kb_err}")
+                    kb_message_suffix = " This event will be added to your knowledge base in the next scheduled sync."
+
+                return {
+                    "status": "success",
+                    "event_id": created.get("id"),
+                    "html_link": created.get("htmlLink"),
+                    "message": f"Successfully created '{final_summary}' on Google Calendar.{kb_message_suffix}",
+                }
 
         except Exception as e:
             from langgraph.errors import GraphInterrupt

surfsense_backend/app/agents/new_chat/tools/google_calendar/delete_event.py

@@ -9,6 +9,7 @@ from langchain_core.tools import tool
 from sqlalchemy.ext.asyncio import AsyncSession
 
 from app.agents.new_chat.tools.hitl import request_approval
+from app.db import async_session_maker
 from app.services.google_calendar import GoogleCalendarToolMetadataService
 
 logger = logging.getLogger(__name__)
@@ -19,6 +20,23 @@ def create_delete_calendar_event_tool(
     search_space_id: int | None = None,
     user_id: str | None = None,
 ):
+    """
+    Factory function to create the delete_calendar_event tool.
+
+    The tool acquires its own short-lived ``AsyncSession`` per call via
+    :data:`async_session_maker` so the closure is safe to share across
+    HTTP requests by the compiled-agent cache. Capturing a per-request
+    session here would surface stale/closed sessions on cache hits.
+
+    Args:
+        db_session: Reserved for registry compatibility. Per-call sessions
+            are opened via :data:`async_session_maker` inside the tool body.
+
+    Returns:
+        Configured delete_calendar_event tool
+    """
+    del db_session  # per-call session — see docstring
+
     @tool
     async def delete_calendar_event(
         event_title_or_id: str,
@@ -54,252 +72,258 @@ def create_delete_calendar_event_tool(
             f"delete_calendar_event called: event_ref='{event_title_or_id}', delete_from_kb={delete_from_kb}"
         )
 
-        if db_session is None or search_space_id is None or user_id is None:
+        if search_space_id is None or user_id is None:
             return {
                 "status": "error",
                 "message": "Google Calendar tool not properly configured. Please contact support.",
             }
 
         try:
-            metadata_service = GoogleCalendarToolMetadataService(db_session)
-            context = await metadata_service.get_deletion_context(
-                search_space_id, user_id, event_title_or_id
-            )
-
-            if "error" in context:
-                error_msg = context["error"]
-                if "not found" in error_msg.lower():
-                    logger.warning(f"Event not found: {error_msg}")
-                    return {"status": "not_found", "message": error_msg}
-                logger.error(f"Failed to fetch deletion context: {error_msg}")
-                return {"status": "error", "message": error_msg}
-
-            account = context.get("account", {})
-            if account.get("auth_expired"):
-                logger.warning(
-                    "Google Calendar account %s has expired authentication",
-                    account.get("id"),
+            async with async_session_maker() as db_session:
+                metadata_service = GoogleCalendarToolMetadataService(db_session)
+                context = await metadata_service.get_deletion_context(
+                    search_space_id, user_id, event_title_or_id
                 )
-                return {
-                    "status": "auth_error",
-                    "message": "The Google Calendar account for this event needs re-authentication. Please re-authenticate in your connector settings.",
-                    "connector_type": "google_calendar",
-                }
 
-            event = context["event"]
-            event_id = event["event_id"]
-            document_id = event.get("document_id")
-            connector_id_from_context = context["account"]["id"]
+                if "error" in context:
+                    error_msg = context["error"]
+                    if "not found" in error_msg.lower():
+                        logger.warning(f"Event not found: {error_msg}")
+                        return {"status": "not_found", "message": error_msg}
+                    logger.error(f"Failed to fetch deletion context: {error_msg}")
+                    return {"status": "error", "message": error_msg}
 
-            if not event_id:
-                return {
-                    "status": "error",
-                    "message": "Event ID is missing from the indexed document. Please re-index the event and try again.",
-                }
+                account = context.get("account", {})
+                if account.get("auth_expired"):
+                    logger.warning(
+                        "Google Calendar account %s has expired authentication",
+                        account.get("id"),
+                    )
+                    return {
+                        "status": "auth_error",
+                        "message": "The Google Calendar account for this event needs re-authentication. Please re-authenticate in your connector settings.",
+                        "connector_type": "google_calendar",
+                    }
 
-            logger.info(
-                f"Requesting approval for deleting calendar event: '{event_title_or_id}' (event_id={event_id}, delete_from_kb={delete_from_kb})"
-            )
-            result = request_approval(
-                action_type="google_calendar_event_deletion",
-                tool_name="delete_calendar_event",
-                params={
-                    "event_id": event_id,
-                    "connector_id": connector_id_from_context,
-                    "delete_from_kb": delete_from_kb,
-                },
-                context=context,
-            )
+                event = context["event"]
+                event_id = event["event_id"]
+                document_id = event.get("document_id")
+                connector_id_from_context = context["account"]["id"]
 
-            if result.rejected:
-                return {
-                    "status": "rejected",
-                    "message": "User declined. The event was not deleted. Do not ask again or suggest alternatives.",
-                }
-
-            final_event_id = result.params.get("event_id", event_id)
-            final_connector_id = result.params.get(
-                "connector_id", connector_id_from_context
-            )
-            final_delete_from_kb = result.params.get("delete_from_kb", delete_from_kb)
-
-            if not final_connector_id:
-                return {
-                    "status": "error",
-                    "message": "No connector found for this event.",
-                }
-
-            from sqlalchemy.future import select
-
-            from app.db import SearchSourceConnector, SearchSourceConnectorType
-
-            _calendar_types = [
-                SearchSourceConnectorType.GOOGLE_CALENDAR_CONNECTOR,
-                SearchSourceConnectorType.COMPOSIO_GOOGLE_CALENDAR_CONNECTOR,
-            ]
-
-            result = await db_session.execute(
-                select(SearchSourceConnector).filter(
-                    SearchSourceConnector.id == final_connector_id,
-                    SearchSourceConnector.search_space_id == search_space_id,
-                    SearchSourceConnector.user_id == user_id,
-                    SearchSourceConnector.connector_type.in_(_calendar_types),
-                )
-            )
-            connector = result.scalars().first()
-            if not connector:
-                return {
-                    "status": "error",
-                    "message": "Selected Google Calendar connector is invalid or has been disconnected.",
-                }
-
-            actual_connector_id = connector.id
-
-            logger.info(
-                f"Deleting calendar event: event_id='{final_event_id}', connector={actual_connector_id}"
-            )
-
-            is_composio_calendar = (
-                connector.connector_type
-                == SearchSourceConnectorType.COMPOSIO_GOOGLE_CALENDAR_CONNECTOR
-            )
-            if is_composio_calendar:
-                cca_id = connector.config.get("composio_connected_account_id")
-                if not cca_id:
+                if not event_id:
                     return {
                         "status": "error",
-                        "message": "Composio connected account ID not found for this connector.",
+                        "message": "Event ID is missing from the indexed document. Please re-index the event and try again.",
                     }
-            else:
-                config_data = dict(connector.config)
 
-                from app.config import config as app_config
-                from app.utils.oauth_security import TokenEncryption
-
-                token_encrypted = config_data.get("_token_encrypted", False)
-                if token_encrypted and app_config.SECRET_KEY:
-                    token_encryption = TokenEncryption(app_config.SECRET_KEY)
-                    for key in ("token", "refresh_token", "client_secret"):
-                        if config_data.get(key):
-                            config_data[key] = token_encryption.decrypt_token(
-                                config_data[key]
-                            )
-
-                exp = config_data.get("expiry", "")
-                if exp:
-                    exp = exp.replace("Z", "")
-
-                creds = Credentials(
-                    token=config_data.get("token"),
-                    refresh_token=config_data.get("refresh_token"),
-                    token_uri=config_data.get("token_uri"),
-                    client_id=config_data.get("client_id"),
-                    client_secret=config_data.get("client_secret"),
-                    scopes=config_data.get("scopes", []),
-                    expiry=datetime.fromisoformat(exp) if exp else None,
+                logger.info(
+                    f"Requesting approval for deleting calendar event: '{event_title_or_id}' (event_id={event_id}, delete_from_kb={delete_from_kb})"
+                )
+                result = request_approval(
+                    action_type="google_calendar_event_deletion",
+                    tool_name="delete_calendar_event",
+                    params={
+                        "event_id": event_id,
+                        "connector_id": connector_id_from_context,
+                        "delete_from_kb": delete_from_kb,
+                    },
+                    context=context,
                 )
 
-            try:
-                if is_composio_calendar:
-                    from app.services.composio_service import ComposioService
-
-                    composio_result = await ComposioService().execute_tool(
-                        connected_account_id=cca_id,
-                        tool_name="GOOGLECALENDAR_DELETE_EVENT",
-                        params={"calendar_id": "primary", "event_id": final_event_id},
-                        entity_id=f"surfsense_{user_id}",
-                    )
-                    if not composio_result.get("success"):
-                        raise RuntimeError(
-                            composio_result.get(
-                                "error", "Unknown Composio Calendar error"
-                            )
-                        )
-                else:
-                    service = await asyncio.get_event_loop().run_in_executor(
-                        None, lambda: build("calendar", "v3", credentials=creds)
-                    )
-                    await asyncio.get_event_loop().run_in_executor(
-                        None,
-                        lambda: (
-                            service.events()
-                            .delete(calendarId="primary", eventId=final_event_id)
-                            .execute()
-                        ),
-                    )
-            except Exception as api_err:
-                from googleapiclient.errors import HttpError
-
-                if isinstance(api_err, HttpError) and api_err.resp.status == 403:
-                    logger.warning(
-                        f"Insufficient permissions for connector {actual_connector_id}: {api_err}"
-                    )
-                    try:
-                        from sqlalchemy.orm.attributes import flag_modified
-
-                        _res = await db_session.execute(
-                            select(SearchSourceConnector).where(
-                                SearchSourceConnector.id == actual_connector_id
-                            )
-                        )
-                        _conn = _res.scalar_one_or_none()
-                        if _conn and not _conn.config.get("auth_expired"):
-                            _conn.config = {**_conn.config, "auth_expired": True}
-                            flag_modified(_conn, "config")
-                            await db_session.commit()
-                    except Exception:
-                        logger.warning(
-                            "Failed to persist auth_expired for connector %s",
-                            actual_connector_id,
-                            exc_info=True,
-                        )
+                if result.rejected:
                     return {
-                        "status": "insufficient_permissions",
-                        "connector_id": actual_connector_id,
-                        "message": "This Google Calendar account needs additional permissions. Please re-authenticate in connector settings.",
+                        "status": "rejected",
+                        "message": "User declined. The event was not deleted. Do not ask again or suggest alternatives.",
                     }
-                raise
 
-            logger.info(f"Calendar event deleted: event_id={final_event_id}")
-
-            delete_result: dict[str, Any] = {
-                "status": "success",
-                "event_id": final_event_id,
-                "message": f"Successfully deleted the calendar event '{event.get('summary', event_title_or_id)}'.",
-            }
-
-            deleted_from_kb = False
-            if final_delete_from_kb and document_id:
-                try:
-                    from app.db import Document
-
-                    doc_result = await db_session.execute(
-                        select(Document).filter(Document.id == document_id)
-                    )
-                    document = doc_result.scalars().first()
-                    if document:
-                        await db_session.delete(document)
-                        await db_session.commit()
-                        deleted_from_kb = True
-                        logger.info(
-                            f"Deleted document {document_id} from knowledge base"
-                        )
-                    else:
-                        logger.warning(f"Document {document_id} not found in KB")
-                except Exception as e:
-                    logger.error(f"Failed to delete document from KB: {e}")
-                    await db_session.rollback()
-                    delete_result["warning"] = (
-                        f"Event deleted, but failed to remove from knowledge base: {e!s}"
-                    )
-
-            delete_result["deleted_from_kb"] = deleted_from_kb
-            if deleted_from_kb:
-                delete_result["message"] = (
-                    f"{delete_result.get('message', '')} (also removed from knowledge base)"
+                final_event_id = result.params.get("event_id", event_id)
+                final_connector_id = result.params.get(
+                    "connector_id", connector_id_from_context
+                )
+                final_delete_from_kb = result.params.get(
+                    "delete_from_kb", delete_from_kb
                 )
 
-            return delete_result
+                if not final_connector_id:
+                    return {
+                        "status": "error",
+                        "message": "No connector found for this event.",
+                    }
+
+                from sqlalchemy.future import select
+
+                from app.db import SearchSourceConnector, SearchSourceConnectorType
+
+                _calendar_types = [
+                    SearchSourceConnectorType.GOOGLE_CALENDAR_CONNECTOR,
+                    SearchSourceConnectorType.COMPOSIO_GOOGLE_CALENDAR_CONNECTOR,
+                ]
+
+                result = await db_session.execute(
+                    select(SearchSourceConnector).filter(
+                        SearchSourceConnector.id == final_connector_id,
+                        SearchSourceConnector.search_space_id == search_space_id,
+                        SearchSourceConnector.user_id == user_id,
+                        SearchSourceConnector.connector_type.in_(_calendar_types),
+                    )
+                )
+                connector = result.scalars().first()
+                if not connector:
+                    return {
+                        "status": "error",
+                        "message": "Selected Google Calendar connector is invalid or has been disconnected.",
+                    }
+
+                actual_connector_id = connector.id
+
+                logger.info(
+                    f"Deleting calendar event: event_id='{final_event_id}', connector={actual_connector_id}"
+                )
+
+                is_composio_calendar = (
+                    connector.connector_type
+                    == SearchSourceConnectorType.COMPOSIO_GOOGLE_CALENDAR_CONNECTOR
+                )
+                if is_composio_calendar:
+                    cca_id = connector.config.get("composio_connected_account_id")
+                    if not cca_id:
+                        return {
+                            "status": "error",
+                            "message": "Composio connected account ID not found for this connector.",
+                        }
+                else:
+                    config_data = dict(connector.config)
+
+                    from app.config import config as app_config
+                    from app.utils.oauth_security import TokenEncryption
+
+                    token_encrypted = config_data.get("_token_encrypted", False)
+                    if token_encrypted and app_config.SECRET_KEY:
+                        token_encryption = TokenEncryption(app_config.SECRET_KEY)
+                        for key in ("token", "refresh_token", "client_secret"):
+                            if config_data.get(key):
+                                config_data[key] = token_encryption.decrypt_token(
+                                    config_data[key]
+                                )
+
+                    exp = config_data.get("expiry", "")
+                    if exp:
+                        exp = exp.replace("Z", "")
+
+                    creds = Credentials(
+                        token=config_data.get("token"),
+                        refresh_token=config_data.get("refresh_token"),
+                        token_uri=config_data.get("token_uri"),
+                        client_id=config_data.get("client_id"),
+                        client_secret=config_data.get("client_secret"),
+                        scopes=config_data.get("scopes", []),
+                        expiry=datetime.fromisoformat(exp) if exp else None,
+                    )
+
+                try:
+                    if is_composio_calendar:
+                        from app.services.composio_service import ComposioService
+
+                        composio_result = await ComposioService().execute_tool(
+                            connected_account_id=cca_id,
+                            tool_name="GOOGLECALENDAR_DELETE_EVENT",
+                            params={
+                                "calendar_id": "primary",
+                                "event_id": final_event_id,
+                            },
+                            entity_id=f"surfsense_{user_id}",
+                        )
+                        if not composio_result.get("success"):
+                            raise RuntimeError(
+                                composio_result.get(
+                                    "error", "Unknown Composio Calendar error"
+                                )
+                            )
+                    else:
+                        service = await asyncio.get_event_loop().run_in_executor(
+                            None, lambda: build("calendar", "v3", credentials=creds)
+                        )
+                        await asyncio.get_event_loop().run_in_executor(
+                            None,
+                            lambda: (
+                                service.events()
+                                .delete(calendarId="primary", eventId=final_event_id)
+                                .execute()
+                            ),
+                        )
+                except Exception as api_err:
+                    from googleapiclient.errors import HttpError
+
+                    if isinstance(api_err, HttpError) and api_err.resp.status == 403:
+                        logger.warning(
+                            f"Insufficient permissions for connector {actual_connector_id}: {api_err}"
+                        )
+                        try:
+                            from sqlalchemy.orm.attributes import flag_modified
+
+                            _res = await db_session.execute(
+                                select(SearchSourceConnector).where(
+                                    SearchSourceConnector.id == actual_connector_id
+                                )
+                            )
+                            _conn = _res.scalar_one_or_none()
+                            if _conn and not _conn.config.get("auth_expired"):
+                                _conn.config = {**_conn.config, "auth_expired": True}
+                                flag_modified(_conn, "config")
+                                await db_session.commit()
+                        except Exception:
+                            logger.warning(
+                                "Failed to persist auth_expired for connector %s",
+                                actual_connector_id,
+                                exc_info=True,
+                            )
+                        return {
+                            "status": "insufficient_permissions",
+                            "connector_id": actual_connector_id,
+                            "message": "This Google Calendar account needs additional permissions. Please re-authenticate in connector settings.",
+                        }
+                    raise
+
+                logger.info(f"Calendar event deleted: event_id={final_event_id}")
+
+                delete_result: dict[str, Any] = {
+                    "status": "success",
+                    "event_id": final_event_id,
+                    "message": f"Successfully deleted the calendar event '{event.get('summary', event_title_or_id)}'.",
+                }
+
+                deleted_from_kb = False
+                if final_delete_from_kb and document_id:
+                    try:
+                        from app.db import Document
+
+                        doc_result = await db_session.execute(
+                            select(Document).filter(Document.id == document_id)
+                        )
+                        document = doc_result.scalars().first()
+                        if document:
+                            await db_session.delete(document)
+                            await db_session.commit()
+                            deleted_from_kb = True
+                            logger.info(
+                                f"Deleted document {document_id} from knowledge base"
+                            )
+                        else:
+                            logger.warning(f"Document {document_id} not found in KB")
+                    except Exception as e:
+                        logger.error(f"Failed to delete document from KB: {e}")
+                        await db_session.rollback()
+                        delete_result["warning"] = (
+                            f"Event deleted, but failed to remove from knowledge base: {e!s}"
+                        )
+
+                delete_result["deleted_from_kb"] = deleted_from_kb
+                if deleted_from_kb:
+                    delete_result["message"] = (
+                        f"{delete_result.get('message', '')} (also removed from knowledge base)"
+                    )
+
+                return delete_result
 
         except Exception as e:
             from langgraph.errors import GraphInterrupt

surfsense_backend/app/agents/new_chat/tools/google_calendar/search_events.py

@@ -6,7 +6,7 @@ from sqlalchemy.ext.asyncio import AsyncSession
 from sqlalchemy.future import select
 
 from app.agents.new_chat.tools.gmail.search_emails import _build_credentials
-from app.db import SearchSourceConnector, SearchSourceConnectorType
+from app.db import SearchSourceConnector, SearchSourceConnectorType, async_session_maker
 
 logger = logging.getLogger(__name__)
 
@@ -50,6 +50,23 @@ def create_search_calendar_events_tool(
     search_space_id: int | None = None,
     user_id: str | None = None,
 ):
+    """
+    Factory function to create the search_calendar_events tool.
+
+    The tool acquires its own short-lived ``AsyncSession`` per call via
+    :data:`async_session_maker` so the closure is safe to share across
+    HTTP requests by the compiled-agent cache. Capturing a per-request
+    session here would surface stale/closed sessions on cache hits.
+
+    Args:
+        db_session: Reserved for registry compatibility. Per-call sessions
+            are opened via :data:`async_session_maker` inside the tool body.
+
+    Returns:
+        Configured search_calendar_events tool
+    """
+    del db_session  # per-call session — see docstring
+
     @tool
     async def search_calendar_events(
         start_date: str,
@@ -67,7 +84,7 @@ def create_search_calendar_events_tool(
             Dictionary with status and a list of events including
             event_id, summary, start, end, location, attendees.
         """
-        if db_session is None or search_space_id is None or user_id is None:
+        if search_space_id is None or user_id is None:
             return {
                 "status": "error",
                 "message": "Calendar tool not properly configured.",
@@ -76,84 +93,85 @@ def create_search_calendar_events_tool(
         max_results = min(max_results, 50)
 
         try:
-            result = await db_session.execute(
-                select(SearchSourceConnector).filter(
-                    SearchSourceConnector.search_space_id == search_space_id,
-                    SearchSourceConnector.user_id == user_id,
-                    SearchSourceConnector.connector_type.in_(_CALENDAR_TYPES),
+            async with async_session_maker() as db_session:
+                result = await db_session.execute(
+                    select(SearchSourceConnector).filter(
+                        SearchSourceConnector.search_space_id == search_space_id,
+                        SearchSourceConnector.user_id == user_id,
+                        SearchSourceConnector.connector_type.in_(_CALENDAR_TYPES),
+                    )
                 )
-            )
-            connector = result.scalars().first()
-            if not connector:
-                return {
-                    "status": "error",
-                    "message": "No Google Calendar connector found. Please connect Google Calendar in your workspace settings.",
-                }
-
-            if (
-                connector.connector_type
-                == SearchSourceConnectorType.COMPOSIO_GOOGLE_CALENDAR_CONNECTOR
-            ):
-                cca_id = connector.config.get("composio_connected_account_id")
-                if not cca_id:
+                connector = result.scalars().first()
+                if not connector:
                     return {
                         "status": "error",
-                        "message": "Composio connected account ID not found for this connector.",
+                        "message": "No Google Calendar connector found. Please connect Google Calendar in your workspace settings.",
                     }
 
-                from app.services.composio_service import ComposioService
-
-                events_raw, error = await ComposioService().get_calendar_events(
-                    connected_account_id=cca_id,
-                    entity_id=f"surfsense_{user_id}",
-                    time_min=_to_calendar_boundary(start_date, is_end=False),
-                    time_max=_to_calendar_boundary(end_date, is_end=True),
-                    max_results=max_results,
-                )
-                if not events_raw and not error:
-                    error = "No events found in the specified date range."
-            else:
-                creds = _build_credentials(connector)
-
-                from app.connectors.google_calendar_connector import (
-                    GoogleCalendarConnector,
-                )
-
-                cal = GoogleCalendarConnector(
-                    credentials=creds,
-                    session=db_session,
-                    user_id=user_id,
-                    connector_id=connector.id,
-                )
-
-                events_raw, error = await cal.get_all_primary_calendar_events(
-                    start_date=start_date,
-                    end_date=end_date,
-                    max_results=max_results,
-                )
-
-            if error:
                 if (
-                    "re-authenticate" in error.lower()
-                    or "authentication failed" in error.lower()
+                    connector.connector_type
+                    == SearchSourceConnectorType.COMPOSIO_GOOGLE_CALENDAR_CONNECTOR
                 ):
-                    return {
-                        "status": "auth_error",
-                        "message": error,
-                        "connector_type": "google_calendar",
-                    }
-                if "no events found" in error.lower():
-                    return {
-                        "status": "success",
-                        "events": [],
-                        "total": 0,
-                        "message": error,
-                    }
-                return {"status": "error", "message": error}
+                    cca_id = connector.config.get("composio_connected_account_id")
+                    if not cca_id:
+                        return {
+                            "status": "error",
+                            "message": "Composio connected account ID not found for this connector.",
+                        }
 
-            events = _format_calendar_events(events_raw)
+                    from app.services.composio_service import ComposioService
 
-            return {"status": "success", "events": events, "total": len(events)}
+                    events_raw, error = await ComposioService().get_calendar_events(
+                        connected_account_id=cca_id,
+                        entity_id=f"surfsense_{user_id}",
+                        time_min=_to_calendar_boundary(start_date, is_end=False),
+                        time_max=_to_calendar_boundary(end_date, is_end=True),
+                        max_results=max_results,
+                    )
+                    if not events_raw and not error:
+                        error = "No events found in the specified date range."
+                else:
+                    creds = _build_credentials(connector)
+
+                    from app.connectors.google_calendar_connector import (
+                        GoogleCalendarConnector,
+                    )
+
+                    cal = GoogleCalendarConnector(
+                        credentials=creds,
+                        session=db_session,
+                        user_id=user_id,
+                        connector_id=connector.id,
+                    )
+
+                    events_raw, error = await cal.get_all_primary_calendar_events(
+                        start_date=start_date,
+                        end_date=end_date,
+                        max_results=max_results,
+                    )
+
+                if error:
+                    if (
+                        "re-authenticate" in error.lower()
+                        or "authentication failed" in error.lower()
+                    ):
+                        return {
+                            "status": "auth_error",
+                            "message": error,
+                            "connector_type": "google_calendar",
+                        }
+                    if "no events found" in error.lower():
+                        return {
+                            "status": "success",
+                            "events": [],
+                            "total": 0,
+                            "message": error,
+                        }
+                    return {"status": "error", "message": error}
+
+                events = _format_calendar_events(events_raw)
+
+                return {"status": "success", "events": events, "total": len(events)}
 
         except Exception as e:
             from langgraph.errors import GraphInterrupt

surfsense_backend/app/agents/new_chat/tools/google_calendar/update_event.py

@@ -9,6 +9,7 @@ from langchain_core.tools import tool
 from sqlalchemy.ext.asyncio import AsyncSession
 
 from app.agents.new_chat.tools.hitl import request_approval
+from app.db import async_session_maker
 from app.services.google_calendar import GoogleCalendarToolMetadataService
 
 logger = logging.getLogger(__name__)
@@ -33,6 +34,23 @@ def create_update_calendar_event_tool(
     search_space_id: int | None = None,
     user_id: str | None = None,
 ):
+    """
+    Factory function to create the update_calendar_event tool.
+
+    The tool acquires its own short-lived ``AsyncSession`` per call via
+    :data:`async_session_maker` so the closure is safe to share across
+    HTTP requests by the compiled-agent cache. Capturing a per-request
+    session here would surface stale/closed sessions on cache hits.
+
+    Args:
+        db_session: Reserved for registry compatibility. Per-call sessions
+            are opened via :data:`async_session_maker` inside the tool body.
+
+    Returns:
+        Configured update_calendar_event tool
+    """
+    del db_session  # per-call session — see docstring
+
     @tool
     async def update_calendar_event(
         event_title_or_id: str,
@@ -74,312 +92,317 @@ def create_update_calendar_event_tool(
         """
         logger.info(f"update_calendar_event called: event_ref='{event_title_or_id}'")
 
-        if db_session is None or search_space_id is None or user_id is None:
+        if search_space_id is None or user_id is None:
             return {
                 "status": "error",
                 "message": "Google Calendar tool not properly configured. Please contact support.",
             }
 
         try:
-            metadata_service = GoogleCalendarToolMetadataService(db_session)
-            context = await metadata_service.get_update_context(
-                search_space_id, user_id, event_title_or_id
-            )
-
-            if "error" in context:
-                error_msg = context["error"]
-                if "not found" in error_msg.lower():
-                    logger.warning(f"Event not found: {error_msg}")
-                    return {"status": "not_found", "message": error_msg}
-                logger.error(f"Failed to fetch update context: {error_msg}")
-                return {"status": "error", "message": error_msg}
-
-            if context.get("auth_expired"):
-                logger.warning("Google Calendar account has expired authentication")
-                return {
-                    "status": "auth_error",
-                    "message": "The Google Calendar account for this event needs re-authentication. Please re-authenticate in your connector settings.",
-                    "connector_type": "google_calendar",
-                }
-
-            event = context["event"]
-            event_id = event["event_id"]
-            document_id = event.get("document_id")
-            connector_id_from_context = context["account"]["id"]
-
-            if not event_id:
-                return {
-                    "status": "error",
-                    "message": "Event ID is missing from the indexed document. Please re-index the event and try again.",
-                }
-
-            logger.info(
-                f"Requesting approval for updating calendar event: '{event_title_or_id}' (event_id={event_id})"
-            )
-            result = request_approval(
-                action_type="google_calendar_event_update",
-                tool_name="update_calendar_event",
-                params={
-                    "event_id": event_id,
-                    "document_id": document_id,
-                    "connector_id": connector_id_from_context,
-                    "new_summary": new_summary,
-                    "new_start_datetime": new_start_datetime,
-                    "new_end_datetime": new_end_datetime,
-                    "new_description": new_description,
-                    "new_location": new_location,
-                    "new_attendees": new_attendees,
-                },
-                context=context,
-            )
-
-            if result.rejected:
-                return {
-                    "status": "rejected",
-                    "message": "User declined. The event was not updated. Do not ask again or suggest alternatives.",
-                }
-
-            final_event_id = result.params.get("event_id", event_id)
-            final_connector_id = result.params.get(
-                "connector_id", connector_id_from_context
-            )
-            final_new_summary = result.params.get("new_summary", new_summary)
-            final_new_start_datetime = result.params.get(
-                "new_start_datetime", new_start_datetime
-            )
-            final_new_end_datetime = result.params.get(
-                "new_end_datetime", new_end_datetime
-            )
-            final_new_description = result.params.get(
-                "new_description", new_description
-            )
-            final_new_location = result.params.get("new_location", new_location)
-            final_new_attendees = result.params.get("new_attendees", new_attendees)
-
-            if not final_connector_id:
-                return {
-                    "status": "error",
-                    "message": "No connector found for this event.",
-                }
-
-            from sqlalchemy.future import select
-
-            from app.db import SearchSourceConnector, SearchSourceConnectorType
-
-            _calendar_types = [
-                SearchSourceConnectorType.GOOGLE_CALENDAR_CONNECTOR,
-                SearchSourceConnectorType.COMPOSIO_GOOGLE_CALENDAR_CONNECTOR,
-            ]
-
-            result = await db_session.execute(
-                select(SearchSourceConnector).filter(
-                    SearchSourceConnector.id == final_connector_id,
-                    SearchSourceConnector.search_space_id == search_space_id,
-                    SearchSourceConnector.user_id == user_id,
-                    SearchSourceConnector.connector_type.in_(_calendar_types),
+            async with async_session_maker() as db_session:
+                metadata_service = GoogleCalendarToolMetadataService(db_session)
+                context = await metadata_service.get_update_context(
+                    search_space_id, user_id, event_title_or_id
                 )
-            )
-            connector = result.scalars().first()
-            if not connector:
-                return {
-                    "status": "error",
-                    "message": "Selected Google Calendar connector is invalid or has been disconnected.",
-                }
 
-            actual_connector_id = connector.id
+                if "error" in context:
+                    error_msg = context["error"]
+                    if "not found" in error_msg.lower():
+                        logger.warning(f"Event not found: {error_msg}")
+                        return {"status": "not_found", "message": error_msg}
+                    logger.error(f"Failed to fetch update context: {error_msg}")
+                    return {"status": "error", "message": error_msg}
 
-            logger.info(
-                f"Updating calendar event: event_id='{final_event_id}', connector={actual_connector_id}"
-            )
+                if context.get("auth_expired"):
+                    logger.warning("Google Calendar account has expired authentication")
+                    return {
+                        "status": "auth_error",
+                        "message": "The Google Calendar account for this event needs re-authentication. Please re-authenticate in your connector settings.",
+                        "connector_type": "google_calendar",
+                    }
 
-            is_composio_calendar = (
-                connector.connector_type
-                == SearchSourceConnectorType.COMPOSIO_GOOGLE_CALENDAR_CONNECTOR
-            )
-            if is_composio_calendar:
-                cca_id = connector.config.get("composio_connected_account_id")
-                if not cca_id:
+                event = context["event"]
+                event_id = event["event_id"]
+                document_id = event.get("document_id")
+                connector_id_from_context = context["account"]["id"]
+
+                if not event_id:
                     return {
                         "status": "error",
-                        "message": "Composio connected account ID not found for this connector.",
+                        "message": "Event ID is missing from the indexed document. Please re-index the event and try again.",
                     }
-            else:
-                config_data = dict(connector.config)
 
-                from app.config import config as app_config
-                from app.utils.oauth_security import TokenEncryption
-
-                token_encrypted = config_data.get("_token_encrypted", False)
-                if token_encrypted and app_config.SECRET_KEY:
-                    token_encryption = TokenEncryption(app_config.SECRET_KEY)
-                    for key in ("token", "refresh_token", "client_secret"):
-                        if config_data.get(key):
-                            config_data[key] = token_encryption.decrypt_token(
-                                config_data[key]
-                            )
-
-                exp = config_data.get("expiry", "")
-                if exp:
-                    exp = exp.replace("Z", "")
-
-                creds = Credentials(
-                    token=config_data.get("token"),
-                    refresh_token=config_data.get("refresh_token"),
-                    token_uri=config_data.get("token_uri"),
-                    client_id=config_data.get("client_id"),
-                    client_secret=config_data.get("client_secret"),
-                    scopes=config_data.get("scopes", []),
-                    expiry=datetime.fromisoformat(exp) if exp else None,
+                logger.info(
+                    f"Requesting approval for updating calendar event: '{event_title_or_id}' (event_id={event_id})"
+                )
+                result = request_approval(
+                    action_type="google_calendar_event_update",
+                    tool_name="update_calendar_event",
+                    params={
+                        "event_id": event_id,
+                        "document_id": document_id,
+                        "connector_id": connector_id_from_context,
+                        "new_summary": new_summary,
+                        "new_start_datetime": new_start_datetime,
+                        "new_end_datetime": new_end_datetime,
+                        "new_description": new_description,
+                        "new_location": new_location,
+                        "new_attendees": new_attendees,
+                    },
+                    context=context,
                 )
 
-            update_body: dict[str, Any] = {}
-            if final_new_summary is not None:
-                update_body["summary"] = final_new_summary
-            if final_new_start_datetime is not None:
-                update_body["start"] = _build_time_body(
-                    final_new_start_datetime, context
+                if result.rejected:
+                    return {
+                        "status": "rejected",
+                        "message": "User declined. The event was not updated. Do not ask again or suggest alternatives.",
+                    }
+
+                final_event_id = result.params.get("event_id", event_id)
+                final_connector_id = result.params.get(
+                    "connector_id", connector_id_from_context
                 )
-            if final_new_end_datetime is not None:
-                update_body["end"] = _build_time_body(final_new_end_datetime, context)
-            if final_new_description is not None:
-                update_body["description"] = final_new_description
-            if final_new_location is not None:
-                update_body["location"] = final_new_location
-            if final_new_attendees is not None:
-                update_body["attendees"] = [
-                    {"email": e.strip()} for e in final_new_attendees if e.strip()
+                final_new_summary = result.params.get("new_summary", new_summary)
+                final_new_start_datetime = result.params.get(
+                    "new_start_datetime", new_start_datetime
+                )
+                final_new_end_datetime = result.params.get(
+                    "new_end_datetime", new_end_datetime
+                )
+                final_new_description = result.params.get(
+                    "new_description", new_description
+                )
+                final_new_location = result.params.get("new_location", new_location)
+                final_new_attendees = result.params.get("new_attendees", new_attendees)
+
+                if not final_connector_id:
+                    return {
+                        "status": "error",
+                        "message": "No connector found for this event.",
+                    }
+
+                from sqlalchemy.future import select
+
+                from app.db import SearchSourceConnector, SearchSourceConnectorType
+
+                _calendar_types = [
+                    SearchSourceConnectorType.GOOGLE_CALENDAR_CONNECTOR,
+                    SearchSourceConnectorType.COMPOSIO_GOOGLE_CALENDAR_CONNECTOR,
                 ]
 
-            if not update_body:
-                return {
-                    "status": "error",
-                    "message": "No changes specified. Please provide at least one field to update.",
-                }
-
-            try:
-                if is_composio_calendar:
-                    from app.services.composio_service import ComposioService
-
-                    composio_params: dict[str, Any] = {
-                        "calendar_id": "primary",
-                        "event_id": final_event_id,
-                    }
-                    if final_new_summary is not None:
-                        composio_params["summary"] = final_new_summary
-                    if final_new_start_datetime is not None:
-                        composio_params["start_time"] = final_new_start_datetime
-                    if final_new_end_datetime is not None:
-                        composio_params["end_time"] = final_new_end_datetime
-                    if final_new_description is not None:
-                        composio_params["description"] = final_new_description
-                    if final_new_location is not None:
-                        composio_params["location"] = final_new_location
-                    if final_new_attendees is not None:
-                        composio_params["attendees"] = [
-                            e.strip() for e in final_new_attendees if e.strip()
-                        ]
-                    if not _is_date_only(
-                        final_new_start_datetime or final_new_end_datetime or ""
-                    ):
-                        composio_params["timezone"] = context.get("timezone", "UTC")
-
-                    composio_result = await ComposioService().execute_tool(
-                        connected_account_id=cca_id,
-                        tool_name="GOOGLECALENDAR_PATCH_EVENT",
-                        params=composio_params,
-                        entity_id=f"surfsense_{user_id}",
+                result = await db_session.execute(
+                    select(SearchSourceConnector).filter(
+                        SearchSourceConnector.id == final_connector_id,
+                        SearchSourceConnector.search_space_id == search_space_id,
+                        SearchSourceConnector.user_id == user_id,
+                        SearchSourceConnector.connector_type.in_(_calendar_types),
                     )
-                    if not composio_result.get("success"):
-                        raise RuntimeError(
-                            composio_result.get(
-                                "error", "Unknown Composio Calendar error"
-                            )
-                        )
-                    updated = composio_result.get("data", {})
-                    if isinstance(updated, dict):
-                        updated = updated.get("data", updated)
-                        if isinstance(updated, dict):
-                            updated = updated.get("response_data", updated)
-                else:
-                    service = await asyncio.get_event_loop().run_in_executor(
-                        None, lambda: build("calendar", "v3", credentials=creds)
-                    )
-                    updated = await asyncio.get_event_loop().run_in_executor(
-                        None,
-                        lambda: (
-                            service.events()
-                            .patch(
-                                calendarId="primary",
-                                eventId=final_event_id,
-                                body=update_body,
-                            )
-                            .execute()
-                        ),
-                    )
-            except Exception as api_err:
-                from googleapiclient.errors import HttpError
-
-                if isinstance(api_err, HttpError) and api_err.resp.status == 403:
-                    logger.warning(
-                        f"Insufficient permissions for connector {actual_connector_id}: {api_err}"
-                    )
-                    try:
-                        from sqlalchemy.orm.attributes import flag_modified
-
-                        _res = await db_session.execute(
-                            select(SearchSourceConnector).where(
-                                SearchSourceConnector.id == actual_connector_id
-                            )
-                        )
-                        _conn = _res.scalar_one_or_none()
-                        if _conn and not _conn.config.get("auth_expired"):
-                            _conn.config = {**_conn.config, "auth_expired": True}
-                            flag_modified(_conn, "config")
-                            await db_session.commit()
-                    except Exception:
-                        logger.warning(
-                            "Failed to persist auth_expired for connector %s",
-                            actual_connector_id,
-                            exc_info=True,
-                        )
+                )
+                connector = result.scalars().first()
+                if not connector:
                     return {
-                        "status": "insufficient_permissions",
-                        "connector_id": actual_connector_id,
-                        "message": "This Google Calendar account needs additional permissions. Please re-authenticate in connector settings.",
+                        "status": "error",
+                        "message": "Selected Google Calendar connector is invalid or has been disconnected.",
                     }
-                raise
 
-            logger.info(f"Calendar event updated: event_id={final_event_id}")
+                actual_connector_id = connector.id
 
-            kb_message_suffix = ""
-            if document_id is not None:
-                try:
-                    from app.services.google_calendar import GoogleCalendarKBSyncService
+                logger.info(
+                    f"Updating calendar event: event_id='{final_event_id}', connector={actual_connector_id}"
+                )
 
-                    kb_service = GoogleCalendarKBSyncService(db_session)
-                    kb_result = await kb_service.sync_after_update(
-                        document_id=document_id,
-                        event_id=final_event_id,
-                        connector_id=actual_connector_id,
-                        search_space_id=search_space_id,
-                        user_id=user_id,
+                is_composio_calendar = (
+                    connector.connector_type
+                    == SearchSourceConnectorType.COMPOSIO_GOOGLE_CALENDAR_CONNECTOR
+                )
+                if is_composio_calendar:
+                    cca_id = connector.config.get("composio_connected_account_id")
+                    if not cca_id:
+                        return {
+                            "status": "error",
+                            "message": "Composio connected account ID not found for this connector.",
+                        }
+                else:
+                    config_data = dict(connector.config)
+
+                    from app.config import config as app_config
+                    from app.utils.oauth_security import TokenEncryption
+
+                    token_encrypted = config_data.get("_token_encrypted", False)
+                    if token_encrypted and app_config.SECRET_KEY:
+                        token_encryption = TokenEncryption(app_config.SECRET_KEY)
+                        for key in ("token", "refresh_token", "client_secret"):
+                            if config_data.get(key):
+                                config_data[key] = token_encryption.decrypt_token(
+                                    config_data[key]
+                                )
+
+                    exp = config_data.get("expiry", "")
+                    if exp:
+                        exp = exp.replace("Z", "")
+
+                    creds = Credentials(
+                        token=config_data.get("token"),
+                        refresh_token=config_data.get("refresh_token"),
+                        token_uri=config_data.get("token_uri"),
+                        client_id=config_data.get("client_id"),
+                        client_secret=config_data.get("client_secret"),
+                        scopes=config_data.get("scopes", []),
+                        expiry=datetime.fromisoformat(exp) if exp else None,
                     )
-                    if kb_result["status"] == "success":
-                        kb_message_suffix = (
-                            " Your knowledge base has also been updated."
-                        )
-                    else:
-                        kb_message_suffix = " The knowledge base will be updated in the next scheduled sync."
-                except Exception as kb_err:
-                    logger.warning(f"KB sync after update failed: {kb_err}")
-                    kb_message_suffix = " The knowledge base will be updated in the next scheduled sync."
 
-            return {
-                "status": "success",
-                "event_id": final_event_id,
-                "html_link": updated.get("htmlLink"),
-                "message": f"Successfully updated the calendar event.{kb_message_suffix}",
-            }
+                update_body: dict[str, Any] = {}
+                if final_new_summary is not None:
+                    update_body["summary"] = final_new_summary
+                if final_new_start_datetime is not None:
+                    update_body["start"] = _build_time_body(
+                        final_new_start_datetime, context
+                    )
+                if final_new_end_datetime is not None:
+                    update_body["end"] = _build_time_body(
+                        final_new_end_datetime, context
+                    )
+                if final_new_description is not None:
+                    update_body["description"] = final_new_description
+                if final_new_location is not None:
+                    update_body["location"] = final_new_location
+                if final_new_attendees is not None:
+                    update_body["attendees"] = [
+                        {"email": e.strip()} for e in final_new_attendees if e.strip()
+                    ]
+
+                if not update_body:
+                    return {
+                        "status": "error",
+                        "message": "No changes specified. Please provide at least one field to update.",
+                    }
+
+                try:
+                    if is_composio_calendar:
+                        from app.services.composio_service import ComposioService
+
+                        composio_params: dict[str, Any] = {
+                            "calendar_id": "primary",
+                            "event_id": final_event_id,
+                        }
+                        if final_new_summary is not None:
+                            composio_params["summary"] = final_new_summary
+                        if final_new_start_datetime is not None:
+                            composio_params["start_time"] = final_new_start_datetime
+                        if final_new_end_datetime is not None:
+                            composio_params["end_time"] = final_new_end_datetime
+                        if final_new_description is not None:
+                            composio_params["description"] = final_new_description
+                        if final_new_location is not None:
+                            composio_params["location"] = final_new_location
+                        if final_new_attendees is not None:
+                            composio_params["attendees"] = [
+                                e.strip() for e in final_new_attendees if e.strip()
+                            ]
+                        if not _is_date_only(
+                            final_new_start_datetime or final_new_end_datetime or ""
+                        ):
+                            composio_params["timezone"] = context.get("timezone", "UTC")
+
+                        composio_result = await ComposioService().execute_tool(
+                            connected_account_id=cca_id,
+                            tool_name="GOOGLECALENDAR_PATCH_EVENT",
+                            params=composio_params,
+                            entity_id=f"surfsense_{user_id}",
+                        )
+                        if not composio_result.get("success"):
+                            raise RuntimeError(
+                                composio_result.get(
+                                    "error", "Unknown Composio Calendar error"
+                                )
+                            )
+                        updated = composio_result.get("data", {})
+                        if isinstance(updated, dict):
+                            updated = updated.get("data", updated)
+                            if isinstance(updated, dict):
+                                updated = updated.get("response_data", updated)
+                    else:
+                        service = await asyncio.get_event_loop().run_in_executor(
+                            None, lambda: build("calendar", "v3", credentials=creds)
+                        )
+                        updated = await asyncio.get_event_loop().run_in_executor(
+                            None,
+                            lambda: (
+                                service.events()
+                                .patch(
+                                    calendarId="primary",
+                                    eventId=final_event_id,
+                                    body=update_body,
+                                )
+                                .execute()
+                            ),
+                        )
+                except Exception as api_err:
+                    from googleapiclient.errors import HttpError
+
+                    if isinstance(api_err, HttpError) and api_err.resp.status == 403:
+                        logger.warning(
+                            f"Insufficient permissions for connector {actual_connector_id}: {api_err}"
+                        )
+                        try:
+                            from sqlalchemy.orm.attributes import flag_modified
+
+                            _res = await db_session.execute(
+                                select(SearchSourceConnector).where(
+                                    SearchSourceConnector.id == actual_connector_id
+                                )
+                            )
+                            _conn = _res.scalar_one_or_none()
+                            if _conn and not _conn.config.get("auth_expired"):
+                                _conn.config = {**_conn.config, "auth_expired": True}
+                                flag_modified(_conn, "config")
+                                await db_session.commit()
+                        except Exception:
+                            logger.warning(
+                                "Failed to persist auth_expired for connector %s",
+                                actual_connector_id,
+                                exc_info=True,
+                            )
+                        return {
+                            "status": "insufficient_permissions",
+                            "connector_id": actual_connector_id,
+                            "message": "This Google Calendar account needs additional permissions. Please re-authenticate in connector settings.",
+                        }
+                    raise
+
+                logger.info(f"Calendar event updated: event_id={final_event_id}")
+
+                kb_message_suffix = ""
+                if document_id is not None:
+                    try:
+                        from app.services.google_calendar import (
+                            GoogleCalendarKBSyncService,
+                        )
+
+                        kb_service = GoogleCalendarKBSyncService(db_session)
+                        kb_result = await kb_service.sync_after_update(
+                            document_id=document_id,
+                            event_id=final_event_id,
+                            connector_id=actual_connector_id,
+                            search_space_id=search_space_id,
+                            user_id=user_id,
+                        )
+                        if kb_result["status"] == "success":
+                            kb_message_suffix = (
+                                " Your knowledge base has also been updated."
+                            )
+                        else:
+                            kb_message_suffix = " The knowledge base will be updated in the next scheduled sync."
+                    except Exception as kb_err:
+                        logger.warning(f"KB sync after update failed: {kb_err}")
+                        kb_message_suffix = " The knowledge base will be updated in the next scheduled sync."
+
+                return {
+                    "status": "success",
+                    "event_id": final_event_id,
+                    "html_link": updated.get("htmlLink"),
+                    "message": f"Successfully updated the calendar event.{kb_message_suffix}",
+                }
 
         except Exception as e:
             from langgraph.errors import GraphInterrupt

surfsense_backend/app/agents/new_chat/tools/google_drive/create_file.py

@@ -8,6 +8,7 @@ from sqlalchemy.ext.asyncio import AsyncSession
 from app.agents.new_chat.tools.hitl import request_approval
 from app.connectors.google_drive.client import GoogleDriveClient
 from app.connectors.google_drive.file_types import GOOGLE_DOC, GOOGLE_SHEET
+from app.db import async_session_maker
 from app.services.google_drive import GoogleDriveToolMetadataService
 
 logger = logging.getLogger(__name__)
@@ -23,6 +24,25 @@ def create_create_google_drive_file_tool(
     search_space_id: int | None = None,
     user_id: str | None = None,
 ):
+    """
+    Factory function to create the create_google_drive_file tool.
+
+    The tool acquires its own short-lived ``AsyncSession`` per call via
+    :data:`async_session_maker` so the closure is safe to share across
+    HTTP requests by the compiled-agent cache. Capturing a per-request
+    session here would surface stale/closed sessions on cache hits.
+
+    Args:
+        db_session: Reserved for registry compatibility. Per-call sessions
+            are opened via :data:`async_session_maker` inside the tool body.
+        search_space_id: Search space ID to find the Google Drive connector
+        user_id: User ID for fetching user-specific context
+
+    Returns:
+        Configured create_google_drive_file tool
+    """
+    del db_session  # per-call session — see docstring
+
     @tool
     async def create_google_drive_file(
         name: str,
@@ -65,7 +85,7 @@ def create_create_google_drive_file_tool(
             f"create_google_drive_file called: name='{name}', type='{file_type}'"
         )
 
-        if db_session is None or search_space_id is None or user_id is None:
+        if search_space_id is None or user_id is None:
             return {
                 "status": "error",
                 "message": "Google Drive tool not properly configured. Please contact support.",
@@ -78,225 +98,232 @@ def create_create_google_drive_file_tool(
             }
 
         try:
-            metadata_service = GoogleDriveToolMetadataService(db_session)
-            context = await metadata_service.get_creation_context(
-                search_space_id, user_id
-            )
-
-            if "error" in context:
-                logger.error(f"Failed to fetch creation context: {context['error']}")
-                return {"status": "error", "message": context["error"]}
-
-            accounts = context.get("accounts", [])
-            if accounts and all(a.get("auth_expired") for a in accounts):
-                logger.warning("All Google Drive accounts have expired authentication")
-                return {
-                    "status": "auth_error",
-                    "message": "All connected Google Drive accounts need re-authentication. Please re-authenticate in your connector settings.",
-                    "connector_type": "google_drive",
-                }
-
-            logger.info(
-                f"Requesting approval for creating Google Drive file: name='{name}', type='{file_type}'"
-            )
-            result = request_approval(
-                action_type="google_drive_file_creation",
-                tool_name="create_google_drive_file",
-                params={
-                    "name": name,
-                    "file_type": file_type,
-                    "content": content,
-                    "connector_id": None,
-                    "parent_folder_id": None,
-                },
-                context=context,
-            )
-
-            if result.rejected:
-                return {
-                    "status": "rejected",
-                    "message": "User declined. The file was not created. Do not ask again or suggest alternatives.",
-                }
-
-            final_name = result.params.get("name", name)
-            final_file_type = result.params.get("file_type", file_type)
-            final_content = result.params.get("content", content)
-            final_connector_id = result.params.get("connector_id")
-            final_parent_folder_id = result.params.get("parent_folder_id")
-
-            if not final_name or not final_name.strip():
-                return {"status": "error", "message": "File name cannot be empty."}
-
-            mime_type = _MIME_MAP.get(final_file_type)
-            if not mime_type:
-                return {
-                    "status": "error",
-                    "message": f"Unsupported file type '{final_file_type}'.",
-                }
-
-            from sqlalchemy.future import select
-
-            from app.db import SearchSourceConnector, SearchSourceConnectorType
-
-            _drive_types = [
-                SearchSourceConnectorType.GOOGLE_DRIVE_CONNECTOR,
-                SearchSourceConnectorType.COMPOSIO_GOOGLE_DRIVE_CONNECTOR,
-            ]
-
-            if final_connector_id is not None:
-                result = await db_session.execute(
-                    select(SearchSourceConnector).filter(
-                        SearchSourceConnector.id == final_connector_id,
-                        SearchSourceConnector.search_space_id == search_space_id,
-                        SearchSourceConnector.user_id == user_id,
-                        SearchSourceConnector.connector_type.in_(_drive_types),
-                    )
+            async with async_session_maker() as db_session:
+                metadata_service = GoogleDriveToolMetadataService(db_session)
+                context = await metadata_service.get_creation_context(
+                    search_space_id, user_id
                 )
-                connector = result.scalars().first()
-                if not connector:
-                    return {
-                        "status": "error",
-                        "message": "Selected Google Drive connector is invalid or has been disconnected.",
-                    }
-                actual_connector_id = connector.id
-            else:
-                result = await db_session.execute(
-                    select(SearchSourceConnector).filter(
-                        SearchSourceConnector.search_space_id == search_space_id,
-                        SearchSourceConnector.user_id == user_id,
-                        SearchSourceConnector.connector_type.in_(_drive_types),
+
+                if "error" in context:
+                    logger.error(
+                        f"Failed to fetch creation context: {context['error']}"
                     )
-                )
-                connector = result.scalars().first()
-                if not connector:
-                    return {
-                        "status": "error",
-                        "message": "No Google Drive connector found. Please connect Google Drive in your workspace settings.",
-                    }
-                actual_connector_id = connector.id
+                    return {"status": "error", "message": context["error"]}
 
-            logger.info(
-                f"Creating Google Drive file: name='{final_name}', type='{final_file_type}', connector={actual_connector_id}"
-            )
-
-            is_composio_drive = (
-                connector.connector_type
-                == SearchSourceConnectorType.COMPOSIO_GOOGLE_DRIVE_CONNECTOR
-            )
-            if is_composio_drive:
-                cca_id = connector.config.get("composio_connected_account_id")
-                if not cca_id:
-                    return {
-                        "status": "error",
-                        "message": "Composio connected account ID not found for this Drive connector.",
-                    }
-            client = GoogleDriveClient(
-                session=db_session,
-                connector_id=actual_connector_id,
-            )
-            try:
-                if is_composio_drive:
-                    from app.services.composio_service import ComposioService
-
-                    params: dict[str, Any] = {
-                        "name": final_name,
-                        "mimeType": mime_type,
-                        "fields": "id,name,webViewLink,mimeType",
-                    }
-                    if final_parent_folder_id:
-                        params["parents"] = [final_parent_folder_id]
-                    if final_content:
-                        params["description"] = final_content[:4096]
-
-                    result = await ComposioService().execute_tool(
-                        connected_account_id=cca_id,
-                        tool_name="GOOGLEDRIVE_CREATE_FILE",
-                        params=params,
-                        entity_id=f"surfsense_{user_id}",
-                    )
-                    if not result.get("success"):
-                        raise RuntimeError(
-                            result.get("error", "Unknown Composio Drive error")
-                        )
-                    created = result.get("data", {})
-                    if isinstance(created, dict):
-                        created = created.get("data", created)
-                        if isinstance(created, dict):
-                            created = created.get("response_data", created)
-                    if not isinstance(created, dict):
-                        created = {}
-                else:
-                    created = await client.create_file(
-                        name=final_name,
-                        mime_type=mime_type,
-                        parent_folder_id=final_parent_folder_id,
-                        content=final_content,
-                    )
-            except HttpError as http_err:
-                if http_err.resp.status == 403:
+                accounts = context.get("accounts", [])
+                if accounts and all(a.get("auth_expired") for a in accounts):
                     logger.warning(
-                        f"Insufficient permissions for connector {actual_connector_id}: {http_err}"
+                        "All Google Drive accounts have expired authentication"
                     )
-                    try:
-                        from sqlalchemy.orm.attributes import flag_modified
-
-                        _res = await db_session.execute(
-                            select(SearchSourceConnector).where(
-                                SearchSourceConnector.id == actual_connector_id
-                            )
-                        )
-                        _conn = _res.scalar_one_or_none()
-                        if _conn and not _conn.config.get("auth_expired"):
-                            _conn.config = {**_conn.config, "auth_expired": True}
-                            flag_modified(_conn, "config")
-                            await db_session.commit()
-                    except Exception:
-                        logger.warning(
-                            "Failed to persist auth_expired for connector %s",
-                            actual_connector_id,
-                            exc_info=True,
-                        )
                     return {
-                        "status": "insufficient_permissions",
-                        "connector_id": actual_connector_id,
-                        "message": "This Google Drive account needs additional permissions. Please re-authenticate in connector settings.",
+                        "status": "auth_error",
+                        "message": "All connected Google Drive accounts need re-authentication. Please re-authenticate in your connector settings.",
+                        "connector_type": "google_drive",
                     }
-                raise
 
-            logger.info(
-                f"Google Drive file created: id={created.get('id')}, name={created.get('name')}"
-            )
-
-            kb_message_suffix = ""
-            try:
-                from app.services.google_drive import GoogleDriveKBSyncService
-
-                kb_service = GoogleDriveKBSyncService(db_session)
-                kb_result = await kb_service.sync_after_create(
-                    file_id=created.get("id"),
-                    file_name=created.get("name", final_name),
-                    mime_type=mime_type,
-                    web_view_link=created.get("webViewLink"),
-                    content=final_content,
-                    connector_id=actual_connector_id,
-                    search_space_id=search_space_id,
-                    user_id=user_id,
+                logger.info(
+                    f"Requesting approval for creating Google Drive file: name='{name}', type='{file_type}'"
+                )
+                result = request_approval(
+                    action_type="google_drive_file_creation",
+                    tool_name="create_google_drive_file",
+                    params={
+                        "name": name,
+                        "file_type": file_type,
+                        "content": content,
+                        "connector_id": None,
+                        "parent_folder_id": None,
+                    },
+                    context=context,
                 )
-                if kb_result["status"] == "success":
-                    kb_message_suffix = " Your knowledge base has also been updated."
-                else:
-                    kb_message_suffix = " This file will be added to your knowledge base in the next scheduled sync."
-            except Exception as kb_err:
-                logger.warning(f"KB sync after create failed: {kb_err}")
-                kb_message_suffix = " This file will be added to your knowledge base in the next scheduled sync."
 
-            return {
-                "status": "success",
-                "file_id": created.get("id"),
-                "name": created.get("name"),
-                "web_view_link": created.get("webViewLink"),
-                "message": f"Successfully created '{created.get('name')}' in Google Drive.{kb_message_suffix}",
-            }
+                if result.rejected:
+                    return {
+                        "status": "rejected",
+                        "message": "User declined. The file was not created. Do not ask again or suggest alternatives.",
+                    }
+
+                final_name = result.params.get("name", name)
+                final_file_type = result.params.get("file_type", file_type)
+                final_content = result.params.get("content", content)
+                final_connector_id = result.params.get("connector_id")
+                final_parent_folder_id = result.params.get("parent_folder_id")
+
+                if not final_name or not final_name.strip():
+                    return {"status": "error", "message": "File name cannot be empty."}
+
+                mime_type = _MIME_MAP.get(final_file_type)
+                if not mime_type:
+                    return {
+                        "status": "error",
+                        "message": f"Unsupported file type '{final_file_type}'.",
+                    }
+
+                from sqlalchemy.future import select
+
+                from app.db import SearchSourceConnector, SearchSourceConnectorType
+
+                _drive_types = [
+                    SearchSourceConnectorType.GOOGLE_DRIVE_CONNECTOR,
+                    SearchSourceConnectorType.COMPOSIO_GOOGLE_DRIVE_CONNECTOR,
+                ]
+
+                if final_connector_id is not None:
+                    result = await db_session.execute(
+                        select(SearchSourceConnector).filter(
+                            SearchSourceConnector.id == final_connector_id,
+                            SearchSourceConnector.search_space_id == search_space_id,
+                            SearchSourceConnector.user_id == user_id,
+                            SearchSourceConnector.connector_type.in_(_drive_types),
+                        )
+                    )
+                    connector = result.scalars().first()
+                    if not connector:
+                        return {
+                            "status": "error",
+                            "message": "Selected Google Drive connector is invalid or has been disconnected.",
+                        }
+                    actual_connector_id = connector.id
+                else:
+                    result = await db_session.execute(
+                        select(SearchSourceConnector).filter(
+                            SearchSourceConnector.search_space_id == search_space_id,
+                            SearchSourceConnector.user_id == user_id,
+                            SearchSourceConnector.connector_type.in_(_drive_types),
+                        )
+                    )
+                    connector = result.scalars().first()
+                    if not connector:
+                        return {
+                            "status": "error",
+                            "message": "No Google Drive connector found. Please connect Google Drive in your workspace settings.",
+                        }
+                    actual_connector_id = connector.id
+
+                logger.info(
+                    f"Creating Google Drive file: name='{final_name}', type='{final_file_type}', connector={actual_connector_id}"
+                )
+
+                is_composio_drive = (
+                    connector.connector_type
+                    == SearchSourceConnectorType.COMPOSIO_GOOGLE_DRIVE_CONNECTOR
+                )
+                if is_composio_drive:
+                    cca_id = connector.config.get("composio_connected_account_id")
+                    if not cca_id:
+                        return {
+                            "status": "error",
+                            "message": "Composio connected account ID not found for this Drive connector.",
+                        }
+                client = GoogleDriveClient(
+                    session=db_session,
+                    connector_id=actual_connector_id,
+                )
+                try:
+                    if is_composio_drive:
+                        from app.services.composio_service import ComposioService
+
+                        params: dict[str, Any] = {
+                            "name": final_name,
+                            "mimeType": mime_type,
+                            "fields": "id,name,webViewLink,mimeType",
+                        }
+                        if final_parent_folder_id:
+                            params["parents"] = [final_parent_folder_id]
+                        if final_content:
+                            params["description"] = final_content[:4096]
+
+                        result = await ComposioService().execute_tool(
+                            connected_account_id=cca_id,
+                            tool_name="GOOGLEDRIVE_CREATE_FILE",
+                            params=params,
+                            entity_id=f"surfsense_{user_id}",
+                        )
+                        if not result.get("success"):
+                            raise RuntimeError(
+                                result.get("error", "Unknown Composio Drive error")
+                            )
+                        created = result.get("data", {})
+                        if isinstance(created, dict):
+                            created = created.get("data", created)
+                            if isinstance(created, dict):
+                                created = created.get("response_data", created)
+                        if not isinstance(created, dict):
+                            created = {}
+                    else:
+                        created = await client.create_file(
+                            name=final_name,
+                            mime_type=mime_type,
+                            parent_folder_id=final_parent_folder_id,
+                            content=final_content,
+                        )
+                except HttpError as http_err:
+                    if http_err.resp.status == 403:
+                        logger.warning(
+                            f"Insufficient permissions for connector {actual_connector_id}: {http_err}"
+                        )
+                        try:
+                            from sqlalchemy.orm.attributes import flag_modified
+
+                            _res = await db_session.execute(
+                                select(SearchSourceConnector).where(
+                                    SearchSourceConnector.id == actual_connector_id
+                                )
+                            )
+                            _conn = _res.scalar_one_or_none()
+                            if _conn and not _conn.config.get("auth_expired"):
+                                _conn.config = {**_conn.config, "auth_expired": True}
+                                flag_modified(_conn, "config")
+                                await db_session.commit()
+                        except Exception:
+                            logger.warning(
+                                "Failed to persist auth_expired for connector %s",
+                                actual_connector_id,
+                                exc_info=True,
+                            )
+                        return {
+                            "status": "insufficient_permissions",
+                            "connector_id": actual_connector_id,
+                            "message": "This Google Drive account needs additional permissions. Please re-authenticate in connector settings.",
+                        }
+                    raise
+
+                logger.info(
+                    f"Google Drive file created: id={created.get('id')}, name={created.get('name')}"
+                )
+
+                kb_message_suffix = ""
+                try:
+                    from app.services.google_drive import GoogleDriveKBSyncService
+
+                    kb_service = GoogleDriveKBSyncService(db_session)
+                    kb_result = await kb_service.sync_after_create(
+                        file_id=created.get("id"),
+                        file_name=created.get("name", final_name),
+                        mime_type=mime_type,
+                        web_view_link=created.get("webViewLink"),
+                        content=final_content,
+                        connector_id=actual_connector_id,
+                        search_space_id=search_space_id,
+                        user_id=user_id,
+                    )
+                    if kb_result["status"] == "success":
+                        kb_message_suffix = (
+                            " Your knowledge base has also been updated."
+                        )
+                    else:
+                        kb_message_suffix = " This file will be added to your knowledge base in the next scheduled sync."
+                except Exception as kb_err:
+                    logger.warning(f"KB sync after create failed: {kb_err}")
+                    kb_message_suffix = " This file will be added to your knowledge base in the next scheduled sync."
+
+                return {
+                    "status": "success",
+                    "file_id": created.get("id"),
+                    "name": created.get("name"),
+                    "web_view_link": created.get("webViewLink"),
+                    "message": f"Successfully created '{created.get('name')}' in Google Drive.{kb_message_suffix}",
+                }
 
         except Exception as e:
             from langgraph.errors import GraphInterrupt

surfsense_backend/app/agents/new_chat/tools/google_drive/trash_file.py

@@ -7,6 +7,7 @@ from sqlalchemy.ext.asyncio import AsyncSession
 
 from app.agents.new_chat.tools.hitl import request_approval
 from app.connectors.google_drive.client import GoogleDriveClient
+from app.db import async_session_maker
 from app.services.google_drive import GoogleDriveToolMetadataService
 
 logger = logging.getLogger(__name__)
@@ -17,6 +18,25 @@ def create_delete_google_drive_file_tool(
     search_space_id: int | None = None,
     user_id: str | None = None,
 ):
+    """
+    Factory function to create the delete_google_drive_file tool.
+
+    The tool acquires its own short-lived ``AsyncSession`` per call via
+    :data:`async_session_maker` so the closure is safe to share across
+    HTTP requests by the compiled-agent cache. Capturing a per-request
+    session here would surface stale/closed sessions on cache hits.
+
+    Args:
+        db_session: Reserved for registry compatibility. Per-call sessions
+            are opened via :data:`async_session_maker` inside the tool body.
+        search_space_id: Search space ID to find the Google Drive connector
+        user_id: User ID for fetching user-specific context
+
+    Returns:
+        Configured delete_google_drive_file tool
+    """
+    del db_session  # per-call session — see docstring
+
     @tool
     async def delete_google_drive_file(
         file_name: str,
@@ -55,211 +75,214 @@ def create_delete_google_drive_file_tool(
             f"delete_google_drive_file called: file_name='{file_name}', delete_from_kb={delete_from_kb}"
         )
 
-        if db_session is None or search_space_id is None or user_id is None:
+        if search_space_id is None or user_id is None:
             return {
                 "status": "error",
                 "message": "Google Drive tool not properly configured. Please contact support.",
             }
 
         try:
-            metadata_service = GoogleDriveToolMetadataService(db_session)
-            context = await metadata_service.get_trash_context(
-                search_space_id, user_id, file_name
-            )
-
-            if "error" in context:
-                error_msg = context["error"]
-                if "not found" in error_msg.lower():
-                    logger.warning(f"File not found: {error_msg}")
-                    return {"status": "not_found", "message": error_msg}
-                logger.error(f"Failed to fetch trash context: {error_msg}")
-                return {"status": "error", "message": error_msg}
-
-            account = context.get("account", {})
-            if account.get("auth_expired"):
-                logger.warning(
-                    "Google Drive account %s has expired authentication",
-                    account.get("id"),
+            async with async_session_maker() as db_session:
+                metadata_service = GoogleDriveToolMetadataService(db_session)
+                context = await metadata_service.get_trash_context(
+                    search_space_id, user_id, file_name
                 )
-                return {
-                    "status": "auth_error",
-                    "message": "The Google Drive account for this file needs re-authentication. Please re-authenticate in your connector settings.",
-                    "connector_type": "google_drive",
-                }
 
-            file = context["file"]
-            file_id = file["file_id"]
-            document_id = file.get("document_id")
-            connector_id_from_context = context["account"]["id"]
+                if "error" in context:
+                    error_msg = context["error"]
+                    if "not found" in error_msg.lower():
+                        logger.warning(f"File not found: {error_msg}")
+                        return {"status": "not_found", "message": error_msg}
+                    logger.error(f"Failed to fetch trash context: {error_msg}")
+                    return {"status": "error", "message": error_msg}
 
-            if not file_id:
-                return {
-                    "status": "error",
-                    "message": "File ID is missing from the indexed document. Please re-index the file and try again.",
-                }
+                account = context.get("account", {})
+                if account.get("auth_expired"):
+                    logger.warning(
+                        "Google Drive account %s has expired authentication",
+                        account.get("id"),
+                    )
+                    return {
+                        "status": "auth_error",
+                        "message": "The Google Drive account for this file needs re-authentication. Please re-authenticate in your connector settings.",
+                        "connector_type": "google_drive",
+                    }
 
-            logger.info(
-                f"Requesting approval for deleting Google Drive file: '{file_name}' (file_id={file_id}, delete_from_kb={delete_from_kb})"
-            )
-            result = request_approval(
-                action_type="google_drive_file_trash",
-                tool_name="delete_google_drive_file",
-                params={
-                    "file_id": file_id,
-                    "connector_id": connector_id_from_context,
-                    "delete_from_kb": delete_from_kb,
-                },
-                context=context,
-            )
+                file = context["file"]
+                file_id = file["file_id"]
+                document_id = file.get("document_id")
+                connector_id_from_context = context["account"]["id"]
 
-            if result.rejected:
-                return {
-                    "status": "rejected",
-                    "message": "User declined. The file was not trashed. Do not ask again or suggest alternatives.",
-                }
-
-            final_file_id = result.params.get("file_id", file_id)
-            final_connector_id = result.params.get(
-                "connector_id", connector_id_from_context
-            )
-            final_delete_from_kb = result.params.get("delete_from_kb", delete_from_kb)
-
-            if not final_connector_id:
-                return {
-                    "status": "error",
-                    "message": "No connector found for this file.",
-                }
-
-            from sqlalchemy.future import select
-
-            from app.db import SearchSourceConnector, SearchSourceConnectorType
-
-            _drive_types = [
-                SearchSourceConnectorType.GOOGLE_DRIVE_CONNECTOR,
-                SearchSourceConnectorType.COMPOSIO_GOOGLE_DRIVE_CONNECTOR,
-            ]
-
-            result = await db_session.execute(
-                select(SearchSourceConnector).filter(
-                    SearchSourceConnector.id == final_connector_id,
-                    SearchSourceConnector.search_space_id == search_space_id,
-                    SearchSourceConnector.user_id == user_id,
-                    SearchSourceConnector.connector_type.in_(_drive_types),
-                )
-            )
-            connector = result.scalars().first()
-            if not connector:
-                return {
-                    "status": "error",
-                    "message": "Selected Google Drive connector is invalid or has been disconnected.",
-                }
-
-            logger.info(
-                f"Deleting Google Drive file: file_id='{final_file_id}', connector={final_connector_id}"
-            )
-
-            is_composio_drive = (
-                connector.connector_type
-                == SearchSourceConnectorType.COMPOSIO_GOOGLE_DRIVE_CONNECTOR
-            )
-            if is_composio_drive:
-                cca_id = connector.config.get("composio_connected_account_id")
-                if not cca_id:
+                if not file_id:
                     return {
                         "status": "error",
-                        "message": "Composio connected account ID not found for this Drive connector.",
+                        "message": "File ID is missing from the indexed document. Please re-index the file and try again.",
                     }
 
-            client = GoogleDriveClient(
-                session=db_session,
-                connector_id=connector.id,
-            )
-            try:
-                if is_composio_drive:
-                    from app.services.composio_service import ComposioService
-
-                    result = await ComposioService().execute_tool(
-                        connected_account_id=cca_id,
-                        tool_name="GOOGLEDRIVE_TRASH_FILE",
-                        params={"file_id": final_file_id},
-                        entity_id=f"surfsense_{user_id}",
-                    )
-                    if not result.get("success"):
-                        raise RuntimeError(
-                            result.get("error", "Unknown Composio Drive error")
-                        )
-                else:
-                    await client.trash_file(file_id=final_file_id)
-            except HttpError as http_err:
-                if http_err.resp.status == 403:
-                    logger.warning(
-                        f"Insufficient permissions for connector {connector.id}: {http_err}"
-                    )
-                    try:
-                        from sqlalchemy.orm.attributes import flag_modified
-
-                        if not connector.config.get("auth_expired"):
-                            connector.config = {
-                                **connector.config,
-                                "auth_expired": True,
-                            }
-                            flag_modified(connector, "config")
-                            await db_session.commit()
-                    except Exception:
-                        logger.warning(
-                            "Failed to persist auth_expired for connector %s",
-                            connector.id,
-                            exc_info=True,
-                        )
-                    return {
-                        "status": "insufficient_permissions",
-                        "connector_id": connector.id,
-                        "message": "This Google Drive account needs additional permissions. Please re-authenticate in connector settings.",
-                    }
-                raise
-
-            logger.info(
-                f"Google Drive file deleted (moved to trash): file_id={final_file_id}"
-            )
-
-            trash_result: dict[str, Any] = {
-                "status": "success",
-                "file_id": final_file_id,
-                "message": f"Successfully moved '{file['name']}' to trash.",
-            }
-
-            deleted_from_kb = False
-            if final_delete_from_kb and document_id:
-                try:
-                    from app.db import Document
-
-                    doc_result = await db_session.execute(
-                        select(Document).filter(Document.id == document_id)
-                    )
-                    document = doc_result.scalars().first()
-                    if document:
-                        await db_session.delete(document)
-                        await db_session.commit()
-                        deleted_from_kb = True
-                        logger.info(
-                            f"Deleted document {document_id} from knowledge base"
-                        )
-                    else:
-                        logger.warning(f"Document {document_id} not found in KB")
-                except Exception as e:
-                    logger.error(f"Failed to delete document from KB: {e}")
-                    await db_session.rollback()
-                    trash_result["warning"] = (
-                        f"File moved to trash, but failed to remove from knowledge base: {e!s}"
-                    )
-
-            trash_result["deleted_from_kb"] = deleted_from_kb
-            if deleted_from_kb:
-                trash_result["message"] = (
-                    f"{trash_result.get('message', '')} (also removed from knowledge base)"
+                logger.info(
+                    f"Requesting approval for deleting Google Drive file: '{file_name}' (file_id={file_id}, delete_from_kb={delete_from_kb})"
+                )
+                result = request_approval(
+                    action_type="google_drive_file_trash",
+                    tool_name="delete_google_drive_file",
+                    params={
+                        "file_id": file_id,
+                        "connector_id": connector_id_from_context,
+                        "delete_from_kb": delete_from_kb,
+                    },
+                    context=context,
                 )
 
-            return trash_result
+                if result.rejected:
+                    return {
+                        "status": "rejected",
+                        "message": "User declined. The file was not trashed. Do not ask again or suggest alternatives.",
+                    }
+
+                final_file_id = result.params.get("file_id", file_id)
+                final_connector_id = result.params.get(
+                    "connector_id", connector_id_from_context
+                )
+                final_delete_from_kb = result.params.get(
+                    "delete_from_kb", delete_from_kb
+                )
+
+                if not final_connector_id:
+                    return {
+                        "status": "error",
+                        "message": "No connector found for this file.",
+                    }
+
+                from sqlalchemy.future import select
+
+                from app.db import SearchSourceConnector, SearchSourceConnectorType
+
+                _drive_types = [
+                    SearchSourceConnectorType.GOOGLE_DRIVE_CONNECTOR,
+                    SearchSourceConnectorType.COMPOSIO_GOOGLE_DRIVE_CONNECTOR,
+                ]
+
+                result = await db_session.execute(
+                    select(SearchSourceConnector).filter(
+                        SearchSourceConnector.id == final_connector_id,
+                        SearchSourceConnector.search_space_id == search_space_id,
+                        SearchSourceConnector.user_id == user_id,
+                        SearchSourceConnector.connector_type.in_(_drive_types),
+                    )
+                )
+                connector = result.scalars().first()
+                if not connector:
+                    return {
+                        "status": "error",
+                        "message": "Selected Google Drive connector is invalid or has been disconnected.",
+                    }
+
+                logger.info(
+                    f"Deleting Google Drive file: file_id='{final_file_id}', connector={final_connector_id}"
+                )
+
+                is_composio_drive = (
+                    connector.connector_type
+                    == SearchSourceConnectorType.COMPOSIO_GOOGLE_DRIVE_CONNECTOR
+                )
+                if is_composio_drive:
+                    cca_id = connector.config.get("composio_connected_account_id")
+                    if not cca_id:
+                        return {
+                            "status": "error",
+                            "message": "Composio connected account ID not found for this Drive connector.",
+                        }
+
+                client = GoogleDriveClient(
+                    session=db_session,
+                    connector_id=connector.id,
+                )
+                try:
+                    if is_composio_drive:
+                        from app.services.composio_service import ComposioService
+
+                        result = await ComposioService().execute_tool(
+                            connected_account_id=cca_id,
+                            tool_name="GOOGLEDRIVE_TRASH_FILE",
+                            params={"file_id": final_file_id},
+                            entity_id=f"surfsense_{user_id}",
+                        )
+                        if not result.get("success"):
+                            raise RuntimeError(
+                                result.get("error", "Unknown Composio Drive error")
+                            )
+                    else:
+                        await client.trash_file(file_id=final_file_id)
+                except HttpError as http_err:
+                    if http_err.resp.status == 403:
+                        logger.warning(
+                            f"Insufficient permissions for connector {connector.id}: {http_err}"
+                        )
+                        try:
+                            from sqlalchemy.orm.attributes import flag_modified
+
+                            if not connector.config.get("auth_expired"):
+                                connector.config = {
+                                    **connector.config,
+                                    "auth_expired": True,
+                                }
+                                flag_modified(connector, "config")
+                                await db_session.commit()
+                        except Exception:
+                            logger.warning(
+                                "Failed to persist auth_expired for connector %s",
+                                connector.id,
+                                exc_info=True,
+                            )
+                        return {
+                            "status": "insufficient_permissions",
+                            "connector_id": connector.id,
+                            "message": "This Google Drive account needs additional permissions. Please re-authenticate in connector settings.",
+                        }
+                    raise
+
+                logger.info(
+                    f"Google Drive file deleted (moved to trash): file_id={final_file_id}"
+                )
+
+                trash_result: dict[str, Any] = {
+                    "status": "success",
+                    "file_id": final_file_id,
+                    "message": f"Successfully moved '{file['name']}' to trash.",
+                }
+
+                deleted_from_kb = False
+                if final_delete_from_kb and document_id:
+                    try:
+                        from app.db import Document
+
+                        doc_result = await db_session.execute(
+                            select(Document).filter(Document.id == document_id)
+                        )
+                        document = doc_result.scalars().first()
+                        if document:
+                            await db_session.delete(document)
+                            await db_session.commit()
+                            deleted_from_kb = True
+                            logger.info(
+                                f"Deleted document {document_id} from knowledge base"
+                            )
+                        else:
+                            logger.warning(f"Document {document_id} not found in KB")
+                    except Exception as e:
+                        logger.error(f"Failed to delete document from KB: {e}")
+                        await db_session.rollback()
+                        trash_result["warning"] = (
+                            f"File moved to trash, but failed to remove from knowledge base: {e!s}"
+                        )
+
+                trash_result["deleted_from_kb"] = deleted_from_kb
+                if deleted_from_kb:
+                    trash_result["message"] = (
+                        f"{trash_result.get('message', '')} (also removed from knowledge base)"
+                    )
+
+                return trash_result
 
         except Exception as e:
             from langgraph.errors import GraphInterrupt

surfsense_backend/app/agents/new_chat/tools/jira/create_issue.py

@@ -8,6 +8,7 @@ from sqlalchemy.orm.attributes import flag_modified
 
 from app.agents.new_chat.tools.hitl import request_approval
 from app.connectors.jira_history import JiraHistoryConnector
+from app.db import async_session_maker
 from app.services.jira import JiraToolMetadataService
 
 logger = logging.getLogger(__name__)
@@ -19,6 +20,28 @@ def create_create_jira_issue_tool(
     user_id: str | None = None,
     connector_id: int | None = None,
 ):
+    """Factory function to create the create_jira_issue tool.
+
+    The tool acquires its own short-lived ``AsyncSession`` per call via
+    :data:`async_session_maker`. This is critical for the compiled-agent
+    cache: the compiled graph (and therefore this closure) is reused
+    across HTTP requests, so capturing a per-request session here would
+    surface stale/closed sessions on cache hits. Per-call sessions also
+    keep the request's outer transaction free of long-running Jira API
+    blocking.
+
+    Args:
+        db_session: Reserved for registry compatibility. Per-call sessions
+            are opened via :data:`async_session_maker` inside the tool body.
+        search_space_id: Search space ID to find the Jira connector
+        user_id: User ID for fetching user-specific context
+        connector_id: Optional specific connector ID (if known)
+
+    Returns:
+        Configured create_jira_issue tool
+    """
+    del db_session  # per-call session — see docstring
+
     @tool
     async def create_jira_issue(
         project_key: str,
@@ -49,158 +72,167 @@ def create_create_jira_issue_tool(
             f"create_jira_issue called: project_key='{project_key}', summary='{summary}'"
         )
 
-        if db_session is None or search_space_id is None or user_id is None:
+        if search_space_id is None or user_id is None:
             return {"status": "error", "message": "Jira tool not properly configured."}
 
         try:
-            metadata_service = JiraToolMetadataService(db_session)
-            context = await metadata_service.get_creation_context(
-                search_space_id, user_id
-            )
-
-            if "error" in context:
-                return {"status": "error", "message": context["error"]}
-
-            accounts = context.get("accounts", [])
-            if accounts and all(a.get("auth_expired") for a in accounts):
-                return {
-                    "status": "auth_error",
-                    "message": "All connected Jira accounts need re-authentication.",
-                    "connector_type": "jira",
-                }
-
-            result = request_approval(
-                action_type="jira_issue_creation",
-                tool_name="create_jira_issue",
-                params={
-                    "project_key": project_key,
-                    "summary": summary,
-                    "issue_type": issue_type,
-                    "description": description,
-                    "priority": priority,
-                    "connector_id": connector_id,
-                },
-                context=context,
-            )
-
-            if result.rejected:
-                return {
-                    "status": "rejected",
-                    "message": "User declined. Do not retry or suggest alternatives.",
-                }
-
-            final_project_key = result.params.get("project_key", project_key)
-            final_summary = result.params.get("summary", summary)
-            final_issue_type = result.params.get("issue_type", issue_type)
-            final_description = result.params.get("description", description)
-            final_priority = result.params.get("priority", priority)
-            final_connector_id = result.params.get("connector_id", connector_id)
-
-            if not final_summary or not final_summary.strip():
-                return {"status": "error", "message": "Issue summary cannot be empty."}
-            if not final_project_key:
-                return {"status": "error", "message": "A project must be selected."}
-
-            from sqlalchemy.future import select
-
-            from app.db import SearchSourceConnector, SearchSourceConnectorType
-
-            actual_connector_id = final_connector_id
-            if actual_connector_id is None:
-                result = await db_session.execute(
-                    select(SearchSourceConnector).filter(
-                        SearchSourceConnector.search_space_id == search_space_id,
-                        SearchSourceConnector.user_id == user_id,
-                        SearchSourceConnector.connector_type
-                        == SearchSourceConnectorType.JIRA_CONNECTOR,
-                    )
+            async with async_session_maker() as db_session:
+                metadata_service = JiraToolMetadataService(db_session)
+                context = await metadata_service.get_creation_context(
+                    search_space_id, user_id
                 )
-                connector = result.scalars().first()
-                if not connector:
-                    return {"status": "error", "message": "No Jira connector found."}
-                actual_connector_id = connector.id
-            else:
-                result = await db_session.execute(
-                    select(SearchSourceConnector).filter(
-                        SearchSourceConnector.id == actual_connector_id,
-                        SearchSourceConnector.search_space_id == search_space_id,
-                        SearchSourceConnector.user_id == user_id,
-                        SearchSourceConnector.connector_type
-                        == SearchSourceConnectorType.JIRA_CONNECTOR,
-                    )
+
+                if "error" in context:
+                    return {"status": "error", "message": context["error"]}
+
+                accounts = context.get("accounts", [])
+                if accounts and all(a.get("auth_expired") for a in accounts):
+                    return {
+                        "status": "auth_error",
+                        "message": "All connected Jira accounts need re-authentication.",
+                        "connector_type": "jira",
+                    }
+
+                result = request_approval(
+                    action_type="jira_issue_creation",
+                    tool_name="create_jira_issue",
+                    params={
+                        "project_key": project_key,
+                        "summary": summary,
+                        "issue_type": issue_type,
+                        "description": description,
+                        "priority": priority,
+                        "connector_id": connector_id,
+                    },
+                    context=context,
                 )
-                connector = result.scalars().first()
-                if not connector:
+
+                if result.rejected:
+                    return {
+                        "status": "rejected",
+                        "message": "User declined. Do not retry or suggest alternatives.",
+                    }
+
+                final_project_key = result.params.get("project_key", project_key)
+                final_summary = result.params.get("summary", summary)
+                final_issue_type = result.params.get("issue_type", issue_type)
+                final_description = result.params.get("description", description)
+                final_priority = result.params.get("priority", priority)
+                final_connector_id = result.params.get("connector_id", connector_id)
+
+                if not final_summary or not final_summary.strip():
                     return {
                         "status": "error",
-                        "message": "Selected Jira connector is invalid.",
+                        "message": "Issue summary cannot be empty.",
                     }
+                if not final_project_key:
+                    return {"status": "error", "message": "A project must be selected."}
 
-            try:
-                jira_history = JiraHistoryConnector(
-                    session=db_session, connector_id=actual_connector_id
-                )
-                jira_client = await jira_history._get_jira_client()
-                api_result = await asyncio.to_thread(
-                    jira_client.create_issue,
-                    project_key=final_project_key,
-                    summary=final_summary,
-                    issue_type=final_issue_type,
-                    description=final_description,
-                    priority=final_priority,
-                )
-            except Exception as api_err:
-                if "status code 403" in str(api_err).lower():
-                    try:
-                        _conn = connector
-                        _conn.config = {**_conn.config, "auth_expired": True}
-                        flag_modified(_conn, "config")
-                        await db_session.commit()
-                    except Exception:
-                        pass
-                    return {
-                        "status": "insufficient_permissions",
-                        "connector_id": actual_connector_id,
-                        "message": "This Jira account needs additional permissions. Please re-authenticate in connector settings.",
-                    }
-                raise
+                from sqlalchemy.future import select
 
-            issue_key = api_result.get("key", "")
-            issue_url = (
-                f"{jira_history._base_url}/browse/{issue_key}"
-                if jira_history._base_url and issue_key
-                else ""
-            )
+                from app.db import SearchSourceConnector, SearchSourceConnectorType
 
-            kb_message_suffix = ""
-            try:
-                from app.services.jira import JiraKBSyncService
-
-                kb_service = JiraKBSyncService(db_session)
-                kb_result = await kb_service.sync_after_create(
-                    issue_id=issue_key,
-                    issue_identifier=issue_key,
-                    issue_title=final_summary,
-                    description=final_description,
-                    state="To Do",
-                    connector_id=actual_connector_id,
-                    search_space_id=search_space_id,
-                    user_id=user_id,
-                )
-                if kb_result["status"] == "success":
-                    kb_message_suffix = " Your knowledge base has also been updated."
+                actual_connector_id = final_connector_id
+                if actual_connector_id is None:
+                    result = await db_session.execute(
+                        select(SearchSourceConnector).filter(
+                            SearchSourceConnector.search_space_id == search_space_id,
+                            SearchSourceConnector.user_id == user_id,
+                            SearchSourceConnector.connector_type
+                            == SearchSourceConnectorType.JIRA_CONNECTOR,
+                        )
+                    )
+                    connector = result.scalars().first()
+                    if not connector:
+                        return {
+                            "status": "error",
+                            "message": "No Jira connector found.",
+                        }
+                    actual_connector_id = connector.id
                 else:
-                    kb_message_suffix = " This issue will be added to your knowledge base in the next scheduled sync."
-            except Exception as kb_err:
-                logger.warning(f"KB sync after create failed: {kb_err}")
-                kb_message_suffix = " This issue will be added to your knowledge base in the next scheduled sync."
+                    result = await db_session.execute(
+                        select(SearchSourceConnector).filter(
+                            SearchSourceConnector.id == actual_connector_id,
+                            SearchSourceConnector.search_space_id == search_space_id,
+                            SearchSourceConnector.user_id == user_id,
+                            SearchSourceConnector.connector_type
+                            == SearchSourceConnectorType.JIRA_CONNECTOR,
+                        )
+                    )
+                    connector = result.scalars().first()
+                    if not connector:
+                        return {
+                            "status": "error",
+                            "message": "Selected Jira connector is invalid.",
+                        }
 
-            return {
-                "status": "success",
-                "issue_key": issue_key,
-                "issue_url": issue_url,
-                "message": f"Jira issue {issue_key} created successfully.{kb_message_suffix}",
-            }
+                try:
+                    jira_history = JiraHistoryConnector(
+                        session=db_session, connector_id=actual_connector_id
+                    )
+                    jira_client = await jira_history._get_jira_client()
+                    api_result = await asyncio.to_thread(
+                        jira_client.create_issue,
+                        project_key=final_project_key,
+                        summary=final_summary,
+                        issue_type=final_issue_type,
+                        description=final_description,
+                        priority=final_priority,
+                    )
+                except Exception as api_err:
+                    if "status code 403" in str(api_err).lower():
+                        try:
+                            _conn = connector
+                            _conn.config = {**_conn.config, "auth_expired": True}
+                            flag_modified(_conn, "config")
+                            await db_session.commit()
+                        except Exception:
+                            pass
+                        return {
+                            "status": "insufficient_permissions",
+                            "connector_id": actual_connector_id,
+                            "message": "This Jira account needs additional permissions. Please re-authenticate in connector settings.",
+                        }
+                    raise
+
+                issue_key = api_result.get("key", "")
+                issue_url = (
+                    f"{jira_history._base_url}/browse/{issue_key}"
+                    if jira_history._base_url and issue_key
+                    else ""
+                )
+
+                kb_message_suffix = ""
+                try:
+                    from app.services.jira import JiraKBSyncService
+
+                    kb_service = JiraKBSyncService(db_session)
+                    kb_result = await kb_service.sync_after_create(
+                        issue_id=issue_key,
+                        issue_identifier=issue_key,
+                        issue_title=final_summary,
+                        description=final_description,
+                        state="To Do",
+                        connector_id=actual_connector_id,
+                        search_space_id=search_space_id,
+                        user_id=user_id,
+                    )
+                    if kb_result["status"] == "success":
+                        kb_message_suffix = (
+                            " Your knowledge base has also been updated."
+                        )
+                    else:
+                        kb_message_suffix = " This issue will be added to your knowledge base in the next scheduled sync."
+                except Exception as kb_err:
+                    logger.warning(f"KB sync after create failed: {kb_err}")
+                    kb_message_suffix = " This issue will be added to your knowledge base in the next scheduled sync."
+
+                return {
+                    "status": "success",
+                    "issue_key": issue_key,
+                    "issue_url": issue_url,
+                    "message": f"Jira issue {issue_key} created successfully.{kb_message_suffix}",
+                }
 
         except Exception as e:
             from langgraph.errors import GraphInterrupt

surfsense_backend/app/agents/new_chat/tools/jira/delete_issue.py

@@ -8,6 +8,7 @@ from sqlalchemy.orm.attributes import flag_modified
 
 from app.agents.new_chat.tools.hitl import request_approval
 from app.connectors.jira_history import JiraHistoryConnector
+from app.db import async_session_maker
 from app.services.jira import JiraToolMetadataService
 
 logger = logging.getLogger(__name__)
@@ -19,6 +20,26 @@ def create_delete_jira_issue_tool(
     user_id: str | None = None,
     connector_id: int | None = None,
 ):
+    """Factory function to create the delete_jira_issue tool.
+
+    The tool acquires its own short-lived ``AsyncSession`` per call via
+    :data:`async_session_maker`. This is critical for the compiled-agent
+    cache: the compiled graph (and therefore this closure) is reused
+    across HTTP requests, so capturing a per-request session here would
+    surface stale/closed sessions on cache hits.
+
+    Args:
+        db_session: Reserved for registry compatibility. Per-call sessions
+            are opened via :data:`async_session_maker` inside the tool body.
+        search_space_id: Search space ID to find the Jira connector
+        user_id: User ID for fetching user-specific context
+        connector_id: Optional specific connector ID (if known)
+
+    Returns:
+        Configured delete_jira_issue tool
+    """
+    del db_session  # per-call session — see docstring
+
     @tool
     async def delete_jira_issue(
         issue_title_or_key: str,
@@ -44,130 +65,136 @@ def create_delete_jira_issue_tool(
             f"delete_jira_issue called: issue_title_or_key='{issue_title_or_key}'"
         )
 
-        if db_session is None or search_space_id is None or user_id is None:
+        if search_space_id is None or user_id is None:
             return {"status": "error", "message": "Jira tool not properly configured."}
 
         try:
-            metadata_service = JiraToolMetadataService(db_session)
-            context = await metadata_service.get_deletion_context(
-                search_space_id, user_id, issue_title_or_key
-            )
-
-            if "error" in context:
-                error_msg = context["error"]
-                if context.get("auth_expired"):
-                    return {
-                        "status": "auth_error",
-                        "message": error_msg,
-                        "connector_id": context.get("connector_id"),
-                        "connector_type": "jira",
-                    }
-                if "not found" in error_msg.lower():
-                    return {"status": "not_found", "message": error_msg}
-                return {"status": "error", "message": error_msg}
-
-            issue_data = context["issue"]
-            issue_key = issue_data["issue_id"]
-            document_id = issue_data["document_id"]
-            connector_id_from_context = context.get("account", {}).get("id")
-
-            result = request_approval(
-                action_type="jira_issue_deletion",
-                tool_name="delete_jira_issue",
-                params={
-                    "issue_key": issue_key,
-                    "connector_id": connector_id_from_context,
-                    "delete_from_kb": delete_from_kb,
-                },
-                context=context,
-            )
-
-            if result.rejected:
-                return {
-                    "status": "rejected",
-                    "message": "User declined. Do not retry or suggest alternatives.",
-                }
-
-            final_issue_key = result.params.get("issue_key", issue_key)
-            final_connector_id = result.params.get(
-                "connector_id", connector_id_from_context
-            )
-            final_delete_from_kb = result.params.get("delete_from_kb", delete_from_kb)
-
-            from sqlalchemy.future import select
-
-            from app.db import SearchSourceConnector, SearchSourceConnectorType
-
-            if not final_connector_id:
-                return {
-                    "status": "error",
-                    "message": "No connector found for this issue.",
-                }
-
-            result = await db_session.execute(
-                select(SearchSourceConnector).filter(
-                    SearchSourceConnector.id == final_connector_id,
-                    SearchSourceConnector.search_space_id == search_space_id,
-                    SearchSourceConnector.user_id == user_id,
-                    SearchSourceConnector.connector_type
-                    == SearchSourceConnectorType.JIRA_CONNECTOR,
+            async with async_session_maker() as db_session:
+                metadata_service = JiraToolMetadataService(db_session)
+                context = await metadata_service.get_deletion_context(
+                    search_space_id, user_id, issue_title_or_key
                 )
-            )
-            connector = result.scalars().first()
-            if not connector:
-                return {
-                    "status": "error",
-                    "message": "Selected Jira connector is invalid.",
-                }
 
-            try:
-                jira_history = JiraHistoryConnector(
-                    session=db_session, connector_id=final_connector_id
+                if "error" in context:
+                    error_msg = context["error"]
+                    if context.get("auth_expired"):
+                        return {
+                            "status": "auth_error",
+                            "message": error_msg,
+                            "connector_id": context.get("connector_id"),
+                            "connector_type": "jira",
+                        }
+                    if "not found" in error_msg.lower():
+                        return {"status": "not_found", "message": error_msg}
+                    return {"status": "error", "message": error_msg}
+
+                issue_data = context["issue"]
+                issue_key = issue_data["issue_id"]
+                document_id = issue_data["document_id"]
+                connector_id_from_context = context.get("account", {}).get("id")
+
+                result = request_approval(
+                    action_type="jira_issue_deletion",
+                    tool_name="delete_jira_issue",
+                    params={
+                        "issue_key": issue_key,
+                        "connector_id": connector_id_from_context,
+                        "delete_from_kb": delete_from_kb,
+                    },
+                    context=context,
                 )
-                jira_client = await jira_history._get_jira_client()
-                await asyncio.to_thread(jira_client.delete_issue, final_issue_key)
-            except Exception as api_err:
-                if "status code 403" in str(api_err).lower():
-                    try:
-                        connector.config = {**connector.config, "auth_expired": True}
-                        flag_modified(connector, "config")
-                        await db_session.commit()
-                    except Exception:
-                        pass
+
+                if result.rejected:
                     return {
-                        "status": "insufficient_permissions",
-                        "connector_id": final_connector_id,
-                        "message": "This Jira account needs additional permissions. Please re-authenticate in connector settings.",
+                        "status": "rejected",
+                        "message": "User declined. Do not retry or suggest alternatives.",
                     }
-                raise
 
-            deleted_from_kb = False
-            if final_delete_from_kb and document_id:
-                try:
-                    from app.db import Document
+                final_issue_key = result.params.get("issue_key", issue_key)
+                final_connector_id = result.params.get(
+                    "connector_id", connector_id_from_context
+                )
+                final_delete_from_kb = result.params.get(
+                    "delete_from_kb", delete_from_kb
+                )
 
-                    doc_result = await db_session.execute(
-                        select(Document).filter(Document.id == document_id)
+                from sqlalchemy.future import select
+
+                from app.db import SearchSourceConnector, SearchSourceConnectorType
+
+                if not final_connector_id:
+                    return {
+                        "status": "error",
+                        "message": "No connector found for this issue.",
+                    }
+
+                result = await db_session.execute(
+                    select(SearchSourceConnector).filter(
+                        SearchSourceConnector.id == final_connector_id,
+                        SearchSourceConnector.search_space_id == search_space_id,
+                        SearchSourceConnector.user_id == user_id,
+                        SearchSourceConnector.connector_type
+                        == SearchSourceConnectorType.JIRA_CONNECTOR,
                     )
-                    document = doc_result.scalars().first()
-                    if document:
-                        await db_session.delete(document)
-                        await db_session.commit()
-                        deleted_from_kb = True
-                except Exception as e:
-                    logger.error(f"Failed to delete document from KB: {e}")
-                    await db_session.rollback()
+                )
+                connector = result.scalars().first()
+                if not connector:
+                    return {
+                        "status": "error",
+                        "message": "Selected Jira connector is invalid.",
+                    }
 
-            message = f"Jira issue {final_issue_key} deleted successfully."
-            if deleted_from_kb:
-                message += " Also removed from the knowledge base."
+                try:
+                    jira_history = JiraHistoryConnector(
+                        session=db_session, connector_id=final_connector_id
+                    )
+                    jira_client = await jira_history._get_jira_client()
+                    await asyncio.to_thread(jira_client.delete_issue, final_issue_key)
+                except Exception as api_err:
+                    if "status code 403" in str(api_err).lower():
+                        try:
+                            connector.config = {
+                                **connector.config,
+                                "auth_expired": True,
+                            }
+                            flag_modified(connector, "config")
+                            await db_session.commit()
+                        except Exception:
+                            pass
+                        return {
+                            "status": "insufficient_permissions",
+                            "connector_id": final_connector_id,
+                            "message": "This Jira account needs additional permissions. Please re-authenticate in connector settings.",
+                        }
+                    raise
 
-            return {
-                "status": "success",
-                "issue_key": final_issue_key,
-                "deleted_from_kb": deleted_from_kb,
-                "message": message,
-            }
+                deleted_from_kb = False
+                if final_delete_from_kb and document_id:
+                    try:
+                        from app.db import Document
+
+                        doc_result = await db_session.execute(
+                            select(Document).filter(Document.id == document_id)
+                        )
+                        document = doc_result.scalars().first()
+                        if document:
+                            await db_session.delete(document)
+                            await db_session.commit()
+                            deleted_from_kb = True
+                    except Exception as e:
+                        logger.error(f"Failed to delete document from KB: {e}")
+                        await db_session.rollback()
+
+                message = f"Jira issue {final_issue_key} deleted successfully."
+                if deleted_from_kb:
+                    message += " Also removed from the knowledge base."
+
+                return {
+                    "status": "success",
+                    "issue_key": final_issue_key,
+                    "deleted_from_kb": deleted_from_kb,
+                    "message": message,
+                }
 
         except Exception as e:
             from langgraph.errors import GraphInterrupt

surfsense_backend/app/agents/new_chat/tools/jira/update_issue.py

@@ -8,6 +8,7 @@ from sqlalchemy.orm.attributes import flag_modified
 
 from app.agents.new_chat.tools.hitl import request_approval
 from app.connectors.jira_history import JiraHistoryConnector
+from app.db import async_session_maker
 from app.services.jira import JiraToolMetadataService
 
 logger = logging.getLogger(__name__)
@@ -19,6 +20,26 @@ def create_update_jira_issue_tool(
     user_id: str | None = None,
     connector_id: int | None = None,
 ):
+    """Factory function to create the update_jira_issue tool.
+
+    The tool acquires its own short-lived ``AsyncSession`` per call via
+    :data:`async_session_maker`. This is critical for the compiled-agent
+    cache: the compiled graph (and therefore this closure) is reused
+    across HTTP requests, so capturing a per-request session here would
+    surface stale/closed sessions on cache hits.
+
+    Args:
+        db_session: Reserved for registry compatibility. Per-call sessions
+            are opened via :data:`async_session_maker` inside the tool body.
+        search_space_id: Search space ID to find the Jira connector
+        user_id: User ID for fetching user-specific context
+        connector_id: Optional specific connector ID (if known)
+
+    Returns:
+        Configured update_jira_issue tool
+    """
+    del db_session  # per-call session — see docstring
+
     @tool
     async def update_jira_issue(
         issue_title_or_key: str,
@@ -48,169 +69,177 @@ def create_update_jira_issue_tool(
             f"update_jira_issue called: issue_title_or_key='{issue_title_or_key}'"
         )
 
-        if db_session is None or search_space_id is None or user_id is None:
+        if search_space_id is None or user_id is None:
             return {"status": "error", "message": "Jira tool not properly configured."}
 
         try:
-            metadata_service = JiraToolMetadataService(db_session)
-            context = await metadata_service.get_update_context(
-                search_space_id, user_id, issue_title_or_key
-            )
-
-            if "error" in context:
-                error_msg = context["error"]
-                if context.get("auth_expired"):
-                    return {
-                        "status": "auth_error",
-                        "message": error_msg,
-                        "connector_id": context.get("connector_id"),
-                        "connector_type": "jira",
-                    }
-                if "not found" in error_msg.lower():
-                    return {"status": "not_found", "message": error_msg}
-                return {"status": "error", "message": error_msg}
-
-            issue_data = context["issue"]
-            issue_key = issue_data["issue_id"]
-            document_id = issue_data.get("document_id")
-            connector_id_from_context = context.get("account", {}).get("id")
-
-            result = request_approval(
-                action_type="jira_issue_update",
-                tool_name="update_jira_issue",
-                params={
-                    "issue_key": issue_key,
-                    "document_id": document_id,
-                    "new_summary": new_summary,
-                    "new_description": new_description,
-                    "new_priority": new_priority,
-                    "connector_id": connector_id_from_context,
-                },
-                context=context,
-            )
-
-            if result.rejected:
-                return {
-                    "status": "rejected",
-                    "message": "User declined. Do not retry or suggest alternatives.",
-                }
-
-            final_issue_key = result.params.get("issue_key", issue_key)
-            final_summary = result.params.get("new_summary", new_summary)
-            final_description = result.params.get("new_description", new_description)
-            final_priority = result.params.get("new_priority", new_priority)
-            final_connector_id = result.params.get(
-                "connector_id", connector_id_from_context
-            )
-            final_document_id = result.params.get("document_id", document_id)
-
-            from sqlalchemy.future import select
-
-            from app.db import SearchSourceConnector, SearchSourceConnectorType
-
-            if not final_connector_id:
-                return {
-                    "status": "error",
-                    "message": "No connector found for this issue.",
-                }
-
-            result = await db_session.execute(
-                select(SearchSourceConnector).filter(
-                    SearchSourceConnector.id == final_connector_id,
-                    SearchSourceConnector.search_space_id == search_space_id,
-                    SearchSourceConnector.user_id == user_id,
-                    SearchSourceConnector.connector_type
-                    == SearchSourceConnectorType.JIRA_CONNECTOR,
+            async with async_session_maker() as db_session:
+                metadata_service = JiraToolMetadataService(db_session)
+                context = await metadata_service.get_update_context(
+                    search_space_id, user_id, issue_title_or_key
                 )
-            )
-            connector = result.scalars().first()
-            if not connector:
-                return {
-                    "status": "error",
-                    "message": "Selected Jira connector is invalid.",
-                }
 
-            fields: dict[str, Any] = {}
-            if final_summary:
-                fields["summary"] = final_summary
-            if final_description is not None:
-                fields["description"] = {
-                    "type": "doc",
-                    "version": 1,
-                    "content": [
-                        {
-                            "type": "paragraph",
-                            "content": [{"type": "text", "text": final_description}],
+                if "error" in context:
+                    error_msg = context["error"]
+                    if context.get("auth_expired"):
+                        return {
+                            "status": "auth_error",
+                            "message": error_msg,
+                            "connector_id": context.get("connector_id"),
+                            "connector_type": "jira",
                         }
-                    ],
-                }
-            if final_priority:
-                fields["priority"] = {"name": final_priority}
+                    if "not found" in error_msg.lower():
+                        return {"status": "not_found", "message": error_msg}
+                    return {"status": "error", "message": error_msg}
 
-            if not fields:
-                return {"status": "error", "message": "No changes specified."}
+                issue_data = context["issue"]
+                issue_key = issue_data["issue_id"]
+                document_id = issue_data.get("document_id")
+                connector_id_from_context = context.get("account", {}).get("id")
 
-            try:
-                jira_history = JiraHistoryConnector(
-                    session=db_session, connector_id=final_connector_id
+                result = request_approval(
+                    action_type="jira_issue_update",
+                    tool_name="update_jira_issue",
+                    params={
+                        "issue_key": issue_key,
+                        "document_id": document_id,
+                        "new_summary": new_summary,
+                        "new_description": new_description,
+                        "new_priority": new_priority,
+                        "connector_id": connector_id_from_context,
+                    },
+                    context=context,
                 )
-                jira_client = await jira_history._get_jira_client()
-                await asyncio.to_thread(
-                    jira_client.update_issue, final_issue_key, fields
-                )
-            except Exception as api_err:
-                if "status code 403" in str(api_err).lower():
-                    try:
-                        connector.config = {**connector.config, "auth_expired": True}
-                        flag_modified(connector, "config")
-                        await db_session.commit()
-                    except Exception:
-                        pass
+
+                if result.rejected:
                     return {
-                        "status": "insufficient_permissions",
-                        "connector_id": final_connector_id,
-                        "message": "This Jira account needs additional permissions. Please re-authenticate in connector settings.",
+                        "status": "rejected",
+                        "message": "User declined. Do not retry or suggest alternatives.",
                     }
-                raise
 
-            issue_url = (
-                f"{jira_history._base_url}/browse/{final_issue_key}"
-                if jira_history._base_url and final_issue_key
-                else ""
-            )
+                final_issue_key = result.params.get("issue_key", issue_key)
+                final_summary = result.params.get("new_summary", new_summary)
+                final_description = result.params.get(
+                    "new_description", new_description
+                )
+                final_priority = result.params.get("new_priority", new_priority)
+                final_connector_id = result.params.get(
+                    "connector_id", connector_id_from_context
+                )
+                final_document_id = result.params.get("document_id", document_id)
 
-            kb_message_suffix = ""
-            if final_document_id:
-                try:
-                    from app.services.jira import JiraKBSyncService
+                from sqlalchemy.future import select
 
-                    kb_service = JiraKBSyncService(db_session)
-                    kb_result = await kb_service.sync_after_update(
-                        document_id=final_document_id,
-                        issue_id=final_issue_key,
-                        user_id=user_id,
-                        search_space_id=search_space_id,
+                from app.db import SearchSourceConnector, SearchSourceConnectorType
+
+                if not final_connector_id:
+                    return {
+                        "status": "error",
+                        "message": "No connector found for this issue.",
+                    }
+
+                result = await db_session.execute(
+                    select(SearchSourceConnector).filter(
+                        SearchSourceConnector.id == final_connector_id,
+                        SearchSourceConnector.search_space_id == search_space_id,
+                        SearchSourceConnector.user_id == user_id,
+                        SearchSourceConnector.connector_type
+                        == SearchSourceConnectorType.JIRA_CONNECTOR,
                     )
-                    if kb_result["status"] == "success":
-                        kb_message_suffix = (
-                            " Your knowledge base has also been updated."
+                )
+                connector = result.scalars().first()
+                if not connector:
+                    return {
+                        "status": "error",
+                        "message": "Selected Jira connector is invalid.",
+                    }
+
+                fields: dict[str, Any] = {}
+                if final_summary:
+                    fields["summary"] = final_summary
+                if final_description is not None:
+                    fields["description"] = {
+                        "type": "doc",
+                        "version": 1,
+                        "content": [
+                            {
+                                "type": "paragraph",
+                                "content": [
+                                    {"type": "text", "text": final_description}
+                                ],
+                            }
+                        ],
+                    }
+                if final_priority:
+                    fields["priority"] = {"name": final_priority}
+
+                if not fields:
+                    return {"status": "error", "message": "No changes specified."}
+
+                try:
+                    jira_history = JiraHistoryConnector(
+                        session=db_session, connector_id=final_connector_id
+                    )
+                    jira_client = await jira_history._get_jira_client()
+                    await asyncio.to_thread(
+                        jira_client.update_issue, final_issue_key, fields
+                    )
+                except Exception as api_err:
+                    if "status code 403" in str(api_err).lower():
+                        try:
+                            connector.config = {
+                                **connector.config,
+                                "auth_expired": True,
+                            }
+                            flag_modified(connector, "config")
+                            await db_session.commit()
+                        except Exception:
+                            pass
+                        return {
+                            "status": "insufficient_permissions",
+                            "connector_id": final_connector_id,
+                            "message": "This Jira account needs additional permissions. Please re-authenticate in connector settings.",
+                        }
+                    raise
+
+                issue_url = (
+                    f"{jira_history._base_url}/browse/{final_issue_key}"
+                    if jira_history._base_url and final_issue_key
+                    else ""
+                )
+
+                kb_message_suffix = ""
+                if final_document_id:
+                    try:
+                        from app.services.jira import JiraKBSyncService
+
+                        kb_service = JiraKBSyncService(db_session)
+                        kb_result = await kb_service.sync_after_update(
+                            document_id=final_document_id,
+                            issue_id=final_issue_key,
+                            user_id=user_id,
+                            search_space_id=search_space_id,
                         )
-                    else:
+                        if kb_result["status"] == "success":
+                            kb_message_suffix = (
+                                " Your knowledge base has also been updated."
+                            )
+                        else:
+                            kb_message_suffix = (
+                                " The knowledge base will be updated in the next sync."
+                            )
+                    except Exception as kb_err:
+                        logger.warning(f"KB sync after update failed: {kb_err}")
                         kb_message_suffix = (
                             " The knowledge base will be updated in the next sync."
                         )
-                except Exception as kb_err:
-                    logger.warning(f"KB sync after update failed: {kb_err}")
-                    kb_message_suffix = (
-                        " The knowledge base will be updated in the next sync."
-                    )
 
-            return {
-                "status": "success",
-                "issue_key": final_issue_key,
-                "issue_url": issue_url,
-                "message": f"Jira issue {final_issue_key} updated successfully.{kb_message_suffix}",
-            }
+                return {
+                    "status": "success",
+                    "issue_key": final_issue_key,
+                    "issue_url": issue_url,
+                    "message": f"Jira issue {final_issue_key} updated successfully.{kb_message_suffix}",
+                }
 
         except Exception as e:
             from langgraph.errors import GraphInterrupt

surfsense_backend/app/agents/new_chat/tools/linear/create_issue.py

@@ -6,6 +6,7 @@ from sqlalchemy.ext.asyncio import AsyncSession
 
 from app.agents.new_chat.tools.hitl import request_approval
 from app.connectors.linear_connector import LinearAPIError, LinearConnector
+from app.db import async_session_maker
 from app.services.linear import LinearToolMetadataService
 
 logger = logging.getLogger(__name__)
@@ -17,11 +18,17 @@ def create_create_linear_issue_tool(
     user_id: str | None = None,
     connector_id: int | None = None,
 ):
-    """
-    Factory function to create the create_linear_issue tool.
+    """Factory function to create the create_linear_issue tool.
+
+    The tool acquires its own short-lived ``AsyncSession`` per call via
+    :data:`async_session_maker`. This is critical for the compiled-agent
+    cache: the compiled graph (and therefore this closure) is reused
+    across HTTP requests, so capturing a per-request session here would
+    surface stale/closed sessions on cache hits.
 
     Args:
-        db_session: Database session for accessing the Linear connector
+        db_session: Reserved for registry compatibility. Per-call sessions
+            are opened via :data:`async_session_maker` inside the tool body.
         search_space_id: Search space ID to find the Linear connector
         user_id: User ID for fetching user-specific context
         connector_id: Optional specific connector ID (if known)
@@ -29,6 +36,7 @@ def create_create_linear_issue_tool(
     Returns:
         Configured create_linear_issue tool
     """
+    del db_session  # per-call session — see docstring
 
     @tool
     async def create_linear_issue(
@@ -65,7 +73,7 @@ def create_create_linear_issue_tool(
         """
         logger.info(f"create_linear_issue called: title='{title}'")
 
-        if db_session is None or search_space_id is None or user_id is None:
+        if search_space_id is None or user_id is None:
             logger.error(
                 "Linear tool not properly configured - missing required parameters"
             )
@@ -75,160 +83,170 @@ def create_create_linear_issue_tool(
             }
 
         try:
-            metadata_service = LinearToolMetadataService(db_session)
-            context = await metadata_service.get_creation_context(
-                search_space_id, user_id
-            )
-
-            if "error" in context:
-                logger.error(f"Failed to fetch creation context: {context['error']}")
-                return {"status": "error", "message": context["error"]}
-
-            workspaces = context.get("workspaces", [])
-            if workspaces and all(w.get("auth_expired") for w in workspaces):
-                logger.warning("All Linear accounts have expired authentication")
-                return {
-                    "status": "auth_error",
-                    "message": "All connected Linear accounts need re-authentication. Please re-authenticate in your connector settings.",
-                    "connector_type": "linear",
-                }
-
-            logger.info(f"Requesting approval for creating Linear issue: '{title}'")
-            result = request_approval(
-                action_type="linear_issue_creation",
-                tool_name="create_linear_issue",
-                params={
-                    "title": title,
-                    "description": description,
-                    "team_id": None,
-                    "state_id": None,
-                    "assignee_id": None,
-                    "priority": None,
-                    "label_ids": [],
-                    "connector_id": connector_id,
-                },
-                context=context,
-            )
-
-            if result.rejected:
-                logger.info("Linear issue creation rejected by user")
-                return {
-                    "status": "rejected",
-                    "message": "User declined. Do not retry or suggest alternatives.",
-                }
-
-            final_title = result.params.get("title", title)
-            final_description = result.params.get("description", description)
-            final_team_id = result.params.get("team_id")
-            final_state_id = result.params.get("state_id")
-            final_assignee_id = result.params.get("assignee_id")
-            final_priority = result.params.get("priority")
-            final_label_ids = result.params.get("label_ids") or []
-            final_connector_id = result.params.get("connector_id", connector_id)
-
-            if not final_title or not final_title.strip():
-                logger.error("Title is empty or contains only whitespace")
-                return {"status": "error", "message": "Issue title cannot be empty."}
-            if not final_team_id:
-                return {
-                    "status": "error",
-                    "message": "A team must be selected to create an issue.",
-                }
-
-            from sqlalchemy.future import select
-
-            from app.db import SearchSourceConnector, SearchSourceConnectorType
-
-            actual_connector_id = final_connector_id
-            if actual_connector_id is None:
-                result = await db_session.execute(
-                    select(SearchSourceConnector).filter(
-                        SearchSourceConnector.search_space_id == search_space_id,
-                        SearchSourceConnector.user_id == user_id,
-                        SearchSourceConnector.connector_type
-                        == SearchSourceConnectorType.LINEAR_CONNECTOR,
-                    )
+            async with async_session_maker() as db_session:
+                metadata_service = LinearToolMetadataService(db_session)
+                context = await metadata_service.get_creation_context(
+                    search_space_id, user_id
                 )
-                connector = result.scalars().first()
-                if not connector:
+
+                if "error" in context:
+                    logger.error(
+                        f"Failed to fetch creation context: {context['error']}"
+                    )
+                    return {"status": "error", "message": context["error"]}
+
+                workspaces = context.get("workspaces", [])
+                if workspaces and all(w.get("auth_expired") for w in workspaces):
+                    logger.warning("All Linear accounts have expired authentication")
+                    return {
+                        "status": "auth_error",
+                        "message": "All connected Linear accounts need re-authentication. Please re-authenticate in your connector settings.",
+                        "connector_type": "linear",
+                    }
+
+                logger.info(f"Requesting approval for creating Linear issue: '{title}'")
+                result = request_approval(
+                    action_type="linear_issue_creation",
+                    tool_name="create_linear_issue",
+                    params={
+                        "title": title,
+                        "description": description,
+                        "team_id": None,
+                        "state_id": None,
+                        "assignee_id": None,
+                        "priority": None,
+                        "label_ids": [],
+                        "connector_id": connector_id,
+                    },
+                    context=context,
+                )
+
+                if result.rejected:
+                    logger.info("Linear issue creation rejected by user")
+                    return {
+                        "status": "rejected",
+                        "message": "User declined. Do not retry or suggest alternatives.",
+                    }
+
+                final_title = result.params.get("title", title)
+                final_description = result.params.get("description", description)
+                final_team_id = result.params.get("team_id")
+                final_state_id = result.params.get("state_id")
+                final_assignee_id = result.params.get("assignee_id")
+                final_priority = result.params.get("priority")
+                final_label_ids = result.params.get("label_ids") or []
+                final_connector_id = result.params.get("connector_id", connector_id)
+
+                if not final_title or not final_title.strip():
+                    logger.error("Title is empty or contains only whitespace")
                     return {
                         "status": "error",
-                        "message": "No Linear connector found. Please connect Linear in your workspace settings.",
+                        "message": "Issue title cannot be empty.",
                     }
-                actual_connector_id = connector.id
-                logger.info(f"Found Linear connector: id={actual_connector_id}")
-            else:
-                result = await db_session.execute(
-                    select(SearchSourceConnector).filter(
-                        SearchSourceConnector.id == actual_connector_id,
-                        SearchSourceConnector.search_space_id == search_space_id,
-                        SearchSourceConnector.user_id == user_id,
-                        SearchSourceConnector.connector_type
-                        == SearchSourceConnectorType.LINEAR_CONNECTOR,
-                    )
-                )
-                connector = result.scalars().first()
-                if not connector:
+                if not final_team_id:
                     return {
                         "status": "error",
-                        "message": "Selected Linear connector is invalid or has been disconnected.",
+                        "message": "A team must be selected to create an issue.",
                     }
-                logger.info(f"Validated Linear connector: id={actual_connector_id}")
 
-            logger.info(
-                f"Creating Linear issue with final params: title='{final_title}'"
-            )
-            linear_client = LinearConnector(
-                session=db_session, connector_id=actual_connector_id
-            )
-            result = await linear_client.create_issue(
-                team_id=final_team_id,
-                title=final_title,
-                description=final_description,
-                state_id=final_state_id,
-                assignee_id=final_assignee_id,
-                priority=final_priority,
-                label_ids=final_label_ids if final_label_ids else None,
-            )
+                from sqlalchemy.future import select
 
-            if result.get("status") == "error":
-                logger.error(f"Failed to create Linear issue: {result.get('message')}")
-                return {"status": "error", "message": result.get("message")}
+                from app.db import SearchSourceConnector, SearchSourceConnectorType
 
-            logger.info(
-                f"Linear issue created: {result.get('identifier')} - {result.get('title')}"
-            )
-
-            kb_message_suffix = ""
-            try:
-                from app.services.linear import LinearKBSyncService
-
-                kb_service = LinearKBSyncService(db_session)
-                kb_result = await kb_service.sync_after_create(
-                    issue_id=result.get("id"),
-                    issue_identifier=result.get("identifier", ""),
-                    issue_title=result.get("title", final_title),
-                    issue_url=result.get("url"),
-                    description=final_description,
-                    connector_id=actual_connector_id,
-                    search_space_id=search_space_id,
-                    user_id=user_id,
-                )
-                if kb_result["status"] == "success":
-                    kb_message_suffix = " Your knowledge base has also been updated."
+                actual_connector_id = final_connector_id
+                if actual_connector_id is None:
+                    result = await db_session.execute(
+                        select(SearchSourceConnector).filter(
+                            SearchSourceConnector.search_space_id == search_space_id,
+                            SearchSourceConnector.user_id == user_id,
+                            SearchSourceConnector.connector_type
+                            == SearchSourceConnectorType.LINEAR_CONNECTOR,
+                        )
+                    )
+                    connector = result.scalars().first()
+                    if not connector:
+                        return {
+                            "status": "error",
+                            "message": "No Linear connector found. Please connect Linear in your workspace settings.",
+                        }
+                    actual_connector_id = connector.id
+                    logger.info(f"Found Linear connector: id={actual_connector_id}")
                 else:
-                    kb_message_suffix = " This issue will be added to your knowledge base in the next scheduled sync."
-            except Exception as kb_err:
-                logger.warning(f"KB sync after create failed: {kb_err}")
-                kb_message_suffix = " This issue will be added to your knowledge base in the next scheduled sync."
+                    result = await db_session.execute(
+                        select(SearchSourceConnector).filter(
+                            SearchSourceConnector.id == actual_connector_id,
+                            SearchSourceConnector.search_space_id == search_space_id,
+                            SearchSourceConnector.user_id == user_id,
+                            SearchSourceConnector.connector_type
+                            == SearchSourceConnectorType.LINEAR_CONNECTOR,
+                        )
+                    )
+                    connector = result.scalars().first()
+                    if not connector:
+                        return {
+                            "status": "error",
+                            "message": "Selected Linear connector is invalid or has been disconnected.",
+                        }
+                    logger.info(f"Validated Linear connector: id={actual_connector_id}")
 
-            return {
-                "status": "success",
-                "issue_id": result.get("id"),
-                "identifier": result.get("identifier"),
-                "url": result.get("url"),
-                "message": (result.get("message", "") + kb_message_suffix),
-            }
+                logger.info(
+                    f"Creating Linear issue with final params: title='{final_title}'"
+                )
+                linear_client = LinearConnector(
+                    session=db_session, connector_id=actual_connector_id
+                )
+                result = await linear_client.create_issue(
+                    team_id=final_team_id,
+                    title=final_title,
+                    description=final_description,
+                    state_id=final_state_id,
+                    assignee_id=final_assignee_id,
+                    priority=final_priority,
+                    label_ids=final_label_ids if final_label_ids else None,
+                )
+
+                if result.get("status") == "error":
+                    logger.error(
+                        f"Failed to create Linear issue: {result.get('message')}"
+                    )
+                    return {"status": "error", "message": result.get("message")}
+
+                logger.info(
+                    f"Linear issue created: {result.get('identifier')} - {result.get('title')}"
+                )
+
+                kb_message_suffix = ""
+                try:
+                    from app.services.linear import LinearKBSyncService
+
+                    kb_service = LinearKBSyncService(db_session)
+                    kb_result = await kb_service.sync_after_create(
+                        issue_id=result.get("id"),
+                        issue_identifier=result.get("identifier", ""),
+                        issue_title=result.get("title", final_title),
+                        issue_url=result.get("url"),
+                        description=final_description,
+                        connector_id=actual_connector_id,
+                        search_space_id=search_space_id,
+                        user_id=user_id,
+                    )
+                    if kb_result["status"] == "success":
+                        kb_message_suffix = (
+                            " Your knowledge base has also been updated."
+                        )
+                    else:
+                        kb_message_suffix = " This issue will be added to your knowledge base in the next scheduled sync."
+                except Exception as kb_err:
+                    logger.warning(f"KB sync after create failed: {kb_err}")
+                    kb_message_suffix = " This issue will be added to your knowledge base in the next scheduled sync."
+
+                return {
+                    "status": "success",
+                    "issue_id": result.get("id"),
+                    "identifier": result.get("identifier"),
+                    "url": result.get("url"),
+                    "message": (result.get("message", "") + kb_message_suffix),
+                }
 
         except Exception as e:
             from langgraph.errors import GraphInterrupt

surfsense_backend/app/agents/new_chat/tools/linear/delete_issue.py

@@ -6,6 +6,7 @@ from sqlalchemy.ext.asyncio import AsyncSession
 
 from app.agents.new_chat.tools.hitl import request_approval
 from app.connectors.linear_connector import LinearAPIError, LinearConnector
+from app.db import async_session_maker
 from app.services.linear import LinearToolMetadataService
 
 logger = logging.getLogger(__name__)
@@ -17,11 +18,17 @@ def create_delete_linear_issue_tool(
     user_id: str | None = None,
     connector_id: int | None = None,
 ):
-    """
-    Factory function to create the delete_linear_issue tool.
+    """Factory function to create the delete_linear_issue tool.
+
+    The tool acquires its own short-lived ``AsyncSession`` per call via
+    :data:`async_session_maker`. This is critical for the compiled-agent
+    cache: the compiled graph (and therefore this closure) is reused
+    across HTTP requests, so capturing a per-request session here would
+    surface stale/closed sessions on cache hits.
 
     Args:
-        db_session: Database session for accessing the Linear connector
+        db_session: Reserved for registry compatibility. Per-call sessions
+            are opened via :data:`async_session_maker` inside the tool body.
         search_space_id: Search space ID to find the Linear connector
         user_id: User ID for finding the correct Linear connector
         connector_id: Optional specific connector ID (if known)
@@ -29,6 +36,7 @@ def create_delete_linear_issue_tool(
     Returns:
         Configured delete_linear_issue tool
     """
+    del db_session  # per-call session — see docstring
 
     @tool
     async def delete_linear_issue(
@@ -73,7 +81,7 @@ def create_delete_linear_issue_tool(
             f"delete_linear_issue called: issue_ref='{issue_ref}', delete_from_kb={delete_from_kb}"
         )
 
-        if db_session is None or search_space_id is None or user_id is None:
+        if search_space_id is None or user_id is None:
             logger.error(
                 "Linear tool not properly configured - missing required parameters"
             )
@@ -83,149 +91,152 @@ def create_delete_linear_issue_tool(
             }
 
         try:
-            metadata_service = LinearToolMetadataService(db_session)
-            context = await metadata_service.get_delete_context(
-                search_space_id, user_id, issue_ref
-            )
-
-            if "error" in context:
-                error_msg = context["error"]
-                if context.get("auth_expired"):
-                    logger.warning(f"Auth expired for delete context: {error_msg}")
-                    return {
-                        "status": "auth_error",
-                        "message": error_msg,
-                        "connector_id": context.get("connector_id"),
-                        "connector_type": "linear",
-                    }
-                if "not found" in error_msg.lower():
-                    logger.warning(f"Issue not found: {error_msg}")
-                    return {"status": "not_found", "message": error_msg}
-                else:
-                    logger.error(f"Failed to fetch delete context: {error_msg}")
-                    return {"status": "error", "message": error_msg}
-
-            issue_id = context["issue"]["id"]
-            issue_identifier = context["issue"].get("identifier", "")
-            document_id = context["issue"]["document_id"]
-            connector_id_from_context = context.get("workspace", {}).get("id")
-
-            logger.info(
-                f"Requesting approval for deleting Linear issue: '{issue_ref}' "
-                f"(id={issue_id}, delete_from_kb={delete_from_kb})"
-            )
-            result = request_approval(
-                action_type="linear_issue_deletion",
-                tool_name="delete_linear_issue",
-                params={
-                    "issue_id": issue_id,
-                    "connector_id": connector_id_from_context,
-                    "delete_from_kb": delete_from_kb,
-                },
-                context=context,
-            )
-
-            if result.rejected:
-                logger.info("Linear issue deletion rejected by user")
-                return {
-                    "status": "rejected",
-                    "message": "User declined. Do not retry or suggest alternatives.",
-                }
-
-            final_issue_id = result.params.get("issue_id", issue_id)
-            final_connector_id = result.params.get(
-                "connector_id", connector_id_from_context
-            )
-            final_delete_from_kb = result.params.get("delete_from_kb", delete_from_kb)
-
-            logger.info(
-                f"Deleting Linear issue with final params: issue_id={final_issue_id}, "
-                f"connector_id={final_connector_id}, delete_from_kb={final_delete_from_kb}"
-            )
-
-            from sqlalchemy.future import select
-
-            from app.db import SearchSourceConnector, SearchSourceConnectorType
-
-            if final_connector_id:
-                result = await db_session.execute(
-                    select(SearchSourceConnector).filter(
-                        SearchSourceConnector.id == final_connector_id,
-                        SearchSourceConnector.search_space_id == search_space_id,
-                        SearchSourceConnector.user_id == user_id,
-                        SearchSourceConnector.connector_type
-                        == SearchSourceConnectorType.LINEAR_CONNECTOR,
-                    )
+            async with async_session_maker() as db_session:
+                metadata_service = LinearToolMetadataService(db_session)
+                context = await metadata_service.get_delete_context(
+                    search_space_id, user_id, issue_ref
                 )
-                connector = result.scalars().first()
-                if not connector:
-                    logger.error(
-                        f"Invalid connector_id={final_connector_id} for search_space_id={search_space_id}"
+
+                if "error" in context:
+                    error_msg = context["error"]
+                    if context.get("auth_expired"):
+                        logger.warning(f"Auth expired for delete context: {error_msg}")
+                        return {
+                            "status": "auth_error",
+                            "message": error_msg,
+                            "connector_id": context.get("connector_id"),
+                            "connector_type": "linear",
+                        }
+                    if "not found" in error_msg.lower():
+                        logger.warning(f"Issue not found: {error_msg}")
+                        return {"status": "not_found", "message": error_msg}
+                    else:
+                        logger.error(f"Failed to fetch delete context: {error_msg}")
+                        return {"status": "error", "message": error_msg}
+
+                issue_id = context["issue"]["id"]
+                issue_identifier = context["issue"].get("identifier", "")
+                document_id = context["issue"]["document_id"]
+                connector_id_from_context = context.get("workspace", {}).get("id")
+
+                logger.info(
+                    f"Requesting approval for deleting Linear issue: '{issue_ref}' "
+                    f"(id={issue_id}, delete_from_kb={delete_from_kb})"
+                )
+                result = request_approval(
+                    action_type="linear_issue_deletion",
+                    tool_name="delete_linear_issue",
+                    params={
+                        "issue_id": issue_id,
+                        "connector_id": connector_id_from_context,
+                        "delete_from_kb": delete_from_kb,
+                    },
+                    context=context,
+                )
+
+                if result.rejected:
+                    logger.info("Linear issue deletion rejected by user")
+                    return {
+                        "status": "rejected",
+                        "message": "User declined. Do not retry or suggest alternatives.",
+                    }
+
+                final_issue_id = result.params.get("issue_id", issue_id)
+                final_connector_id = result.params.get(
+                    "connector_id", connector_id_from_context
+                )
+                final_delete_from_kb = result.params.get(
+                    "delete_from_kb", delete_from_kb
+                )
+
+                logger.info(
+                    f"Deleting Linear issue with final params: issue_id={final_issue_id}, "
+                    f"connector_id={final_connector_id}, delete_from_kb={final_delete_from_kb}"
+                )
+
+                from sqlalchemy.future import select
+
+                from app.db import SearchSourceConnector, SearchSourceConnectorType
+
+                if final_connector_id:
+                    result = await db_session.execute(
+                        select(SearchSourceConnector).filter(
+                            SearchSourceConnector.id == final_connector_id,
+                            SearchSourceConnector.search_space_id == search_space_id,
+                            SearchSourceConnector.user_id == user_id,
+                            SearchSourceConnector.connector_type
+                            == SearchSourceConnectorType.LINEAR_CONNECTOR,
+                        )
                     )
+                    connector = result.scalars().first()
+                    if not connector:
+                        logger.error(
+                            f"Invalid connector_id={final_connector_id} for search_space_id={search_space_id}"
+                        )
+                        return {
+                            "status": "error",
+                            "message": "Selected Linear connector is invalid or has been disconnected.",
+                        }
+                    actual_connector_id = connector.id
+                    logger.info(f"Validated Linear connector: id={actual_connector_id}")
+                else:
+                    logger.error("No connector found for this issue")
                     return {
                         "status": "error",
-                        "message": "Selected Linear connector is invalid or has been disconnected.",
+                        "message": "No connector found for this issue.",
                     }
-                actual_connector_id = connector.id
-                logger.info(f"Validated Linear connector: id={actual_connector_id}")
-            else:
-                logger.error("No connector found for this issue")
-                return {
-                    "status": "error",
-                    "message": "No connector found for this issue.",
-                }
 
-            linear_client = LinearConnector(
-                session=db_session, connector_id=actual_connector_id
-            )
+                linear_client = LinearConnector(
+                    session=db_session, connector_id=actual_connector_id
+                )
 
-            result = await linear_client.archive_issue(issue_id=final_issue_id)
+                result = await linear_client.archive_issue(issue_id=final_issue_id)
 
-            logger.info(
-                f"archive_issue result: {result.get('status')} - {result.get('message', '')}"
-            )
+                logger.info(
+                    f"archive_issue result: {result.get('status')} - {result.get('message', '')}"
+                )
 
-            deleted_from_kb = False
-            if (
-                result.get("status") == "success"
-                and final_delete_from_kb
-                and document_id
-            ):
-                try:
-                    from app.db import Document
+                deleted_from_kb = False
+                if (
+                    result.get("status") == "success"
+                    and final_delete_from_kb
+                    and document_id
+                ):
+                    try:
+                        from app.db import Document
 
-                    doc_result = await db_session.execute(
-                        select(Document).filter(Document.id == document_id)
-                    )
-                    document = doc_result.scalars().first()
-                    if document:
-                        await db_session.delete(document)
-                        await db_session.commit()
-                        deleted_from_kb = True
-                        logger.info(
-                            f"Deleted document {document_id} from knowledge base"
+                        doc_result = await db_session.execute(
+                            select(Document).filter(Document.id == document_id)
+                        )
+                        document = doc_result.scalars().first()
+                        if document:
+                            await db_session.delete(document)
+                            await db_session.commit()
+                            deleted_from_kb = True
+                            logger.info(
+                                f"Deleted document {document_id} from knowledge base"
+                            )
+                        else:
+                            logger.warning(f"Document {document_id} not found in KB")
+                    except Exception as e:
+                        logger.error(f"Failed to delete document from KB: {e}")
+                        await db_session.rollback()
+                        result["warning"] = (
+                            f"Issue archived in Linear, but failed to remove from knowledge base: {e!s}"
                         )
-                    else:
-                        logger.warning(f"Document {document_id} not found in KB")
-                except Exception as e:
-                    logger.error(f"Failed to delete document from KB: {e}")
-                    await db_session.rollback()
-                    result["warning"] = (
-                        f"Issue archived in Linear, but failed to remove from knowledge base: {e!s}"
-                    )
 
-            if result.get("status") == "success":
-                result["deleted_from_kb"] = deleted_from_kb
-                if issue_identifier:
-                    result["message"] = (
-                        f"Issue {issue_identifier} archived successfully."
-                    )
-                if deleted_from_kb:
-                    result["message"] = (
-                        f"{result.get('message', '')} Also removed from the knowledge base."
-                    )
+                if result.get("status") == "success":
+                    result["deleted_from_kb"] = deleted_from_kb
+                    if issue_identifier:
+                        result["message"] = (
+                            f"Issue {issue_identifier} archived successfully."
+                        )
+                    if deleted_from_kb:
+                        result["message"] = (
+                            f"{result.get('message', '')} Also removed from the knowledge base."
+                        )
 
-            return result
+                return result
 
         except Exception as e:
             from langgraph.errors import GraphInterrupt

surfsense_backend/app/agents/new_chat/tools/linear/update_issue.py

@@ -6,6 +6,7 @@ from sqlalchemy.ext.asyncio import AsyncSession
 
 from app.agents.new_chat.tools.hitl import request_approval
 from app.connectors.linear_connector import LinearAPIError, LinearConnector
+from app.db import async_session_maker
 from app.services.linear import LinearKBSyncService, LinearToolMetadataService
 
 logger = logging.getLogger(__name__)
@@ -17,11 +18,17 @@ def create_update_linear_issue_tool(
     user_id: str | None = None,
     connector_id: int | None = None,
 ):
-    """
-    Factory function to create the update_linear_issue tool.
+    """Factory function to create the update_linear_issue tool.
+
+    The tool acquires its own short-lived ``AsyncSession`` per call via
+    :data:`async_session_maker`. This is critical for the compiled-agent
+    cache: the compiled graph (and therefore this closure) is reused
+    across HTTP requests, so capturing a per-request session here would
+    surface stale/closed sessions on cache hits.
 
     Args:
-        db_session: Database session for accessing the Linear connector
+        db_session: Reserved for registry compatibility. Per-call sessions
+            are opened via :data:`async_session_maker` inside the tool body.
         search_space_id: Search space ID to find the Linear connector
         user_id: User ID for fetching user-specific context
         connector_id: Optional specific connector ID (if known)
@@ -29,6 +36,7 @@ def create_update_linear_issue_tool(
     Returns:
         Configured update_linear_issue tool
     """
+    del db_session  # per-call session — see docstring
 
     @tool
     async def update_linear_issue(
@@ -86,7 +94,7 @@ def create_update_linear_issue_tool(
         """
         logger.info(f"update_linear_issue called: issue_ref='{issue_ref}'")
 
-        if db_session is None or search_space_id is None or user_id is None:
+        if search_space_id is None or user_id is None:
             logger.error(
                 "Linear tool not properly configured - missing required parameters"
             )
@@ -96,176 +104,177 @@ def create_update_linear_issue_tool(
             }
 
         try:
-            metadata_service = LinearToolMetadataService(db_session)
-            context = await metadata_service.get_update_context(
-                search_space_id, user_id, issue_ref
-            )
-
-            if "error" in context:
-                error_msg = context["error"]
-                if context.get("auth_expired"):
-                    logger.warning(f"Auth expired for update context: {error_msg}")
-                    return {
-                        "status": "auth_error",
-                        "message": error_msg,
-                        "connector_id": context.get("connector_id"),
-                        "connector_type": "linear",
-                    }
-                if "not found" in error_msg.lower():
-                    logger.warning(f"Issue not found: {error_msg}")
-                    return {"status": "not_found", "message": error_msg}
-                else:
-                    logger.error(f"Failed to fetch update context: {error_msg}")
-                    return {"status": "error", "message": error_msg}
-
-            issue_id = context["issue"]["id"]
-            document_id = context["issue"]["document_id"]
-            connector_id_from_context = context.get("workspace", {}).get("id")
-
-            team = context.get("team", {})
-            new_state_id = _resolve_state(team, new_state_name)
-            new_assignee_id = _resolve_assignee(team, new_assignee_email)
-            new_label_ids = _resolve_labels(team, new_label_names)
-
-            logger.info(
-                f"Requesting approval for updating Linear issue: '{issue_ref}' (id={issue_id})"
-            )
-            result = request_approval(
-                action_type="linear_issue_update",
-                tool_name="update_linear_issue",
-                params={
-                    "issue_id": issue_id,
-                    "document_id": document_id,
-                    "new_title": new_title,
-                    "new_description": new_description,
-                    "new_state_id": new_state_id,
-                    "new_assignee_id": new_assignee_id,
-                    "new_priority": new_priority,
-                    "new_label_ids": new_label_ids,
-                    "connector_id": connector_id_from_context,
-                },
-                context=context,
-            )
-
-            if result.rejected:
-                logger.info("Linear issue update rejected by user")
-                return {
-                    "status": "rejected",
-                    "message": "User declined. Do not retry or suggest alternatives.",
-                }
-
-            final_issue_id = result.params.get("issue_id", issue_id)
-            final_document_id = result.params.get("document_id", document_id)
-            final_new_title = result.params.get("new_title", new_title)
-            final_new_description = result.params.get(
-                "new_description", new_description
-            )
-            final_new_state_id = result.params.get("new_state_id", new_state_id)
-            final_new_assignee_id = result.params.get(
-                "new_assignee_id", new_assignee_id
-            )
-            final_new_priority = result.params.get("new_priority", new_priority)
-            final_new_label_ids: list[str] | None = result.params.get(
-                "new_label_ids", new_label_ids
-            )
-            final_connector_id = result.params.get(
-                "connector_id", connector_id_from_context
-            )
-
-            if not final_connector_id:
-                logger.error("No connector found for this issue")
-                return {
-                    "status": "error",
-                    "message": "No connector found for this issue.",
-                }
-
-            from sqlalchemy.future import select
-
-            from app.db import SearchSourceConnector, SearchSourceConnectorType
-
-            result = await db_session.execute(
-                select(SearchSourceConnector).filter(
-                    SearchSourceConnector.id == final_connector_id,
-                    SearchSourceConnector.search_space_id == search_space_id,
-                    SearchSourceConnector.user_id == user_id,
-                    SearchSourceConnector.connector_type
-                    == SearchSourceConnectorType.LINEAR_CONNECTOR,
+            async with async_session_maker() as db_session:
+                metadata_service = LinearToolMetadataService(db_session)
+                context = await metadata_service.get_update_context(
+                    search_space_id, user_id, issue_ref
                 )
-            )
-            connector = result.scalars().first()
-            if not connector:
-                logger.error(
-                    f"Invalid connector_id={final_connector_id} for search_space_id={search_space_id}"
-                )
-                return {
-                    "status": "error",
-                    "message": "Selected Linear connector is invalid or has been disconnected.",
-                }
-            logger.info(f"Validated Linear connector: id={final_connector_id}")
 
-            logger.info(
-                f"Updating Linear issue with final params: issue_id={final_issue_id}"
-            )
-            linear_client = LinearConnector(
-                session=db_session, connector_id=final_connector_id
-            )
-            updated_issue = await linear_client.update_issue(
-                issue_id=final_issue_id,
-                title=final_new_title,
-                description=final_new_description,
-                state_id=final_new_state_id,
-                assignee_id=final_new_assignee_id,
-                priority=final_new_priority,
-                label_ids=final_new_label_ids,
-            )
+                if "error" in context:
+                    error_msg = context["error"]
+                    if context.get("auth_expired"):
+                        logger.warning(f"Auth expired for update context: {error_msg}")
+                        return {
+                            "status": "auth_error",
+                            "message": error_msg,
+                            "connector_id": context.get("connector_id"),
+                            "connector_type": "linear",
+                        }
+                    if "not found" in error_msg.lower():
+                        logger.warning(f"Issue not found: {error_msg}")
+                        return {"status": "not_found", "message": error_msg}
+                    else:
+                        logger.error(f"Failed to fetch update context: {error_msg}")
+                        return {"status": "error", "message": error_msg}
 
-            if updated_issue.get("status") == "error":
-                logger.error(
-                    f"Failed to update Linear issue: {updated_issue.get('message')}"
-                )
-                return {
-                    "status": "error",
-                    "message": updated_issue.get("message"),
-                }
+                issue_id = context["issue"]["id"]
+                document_id = context["issue"]["document_id"]
+                connector_id_from_context = context.get("workspace", {}).get("id")
 
-            logger.info(
-                f"update_issue result: {updated_issue.get('identifier')} - {updated_issue.get('title')}"
-            )
+                team = context.get("team", {})
+                new_state_id = _resolve_state(team, new_state_name)
+                new_assignee_id = _resolve_assignee(team, new_assignee_email)
+                new_label_ids = _resolve_labels(team, new_label_names)
 
-            if final_document_id is not None:
                 logger.info(
-                    f"Updating knowledge base for document {final_document_id}..."
+                    f"Requesting approval for updating Linear issue: '{issue_ref}' (id={issue_id})"
                 )
-                kb_service = LinearKBSyncService(db_session)
-                kb_result = await kb_service.sync_after_update(
-                    document_id=final_document_id,
-                    issue_id=final_issue_id,
-                    user_id=user_id,
-                    search_space_id=search_space_id,
+                result = request_approval(
+                    action_type="linear_issue_update",
+                    tool_name="update_linear_issue",
+                    params={
+                        "issue_id": issue_id,
+                        "document_id": document_id,
+                        "new_title": new_title,
+                        "new_description": new_description,
+                        "new_state_id": new_state_id,
+                        "new_assignee_id": new_assignee_id,
+                        "new_priority": new_priority,
+                        "new_label_ids": new_label_ids,
+                        "connector_id": connector_id_from_context,
+                    },
+                    context=context,
                 )
-                if kb_result["status"] == "success":
-                    logger.info(
-                        f"Knowledge base successfully updated for issue {final_issue_id}"
-                    )
-                    kb_message = " Your knowledge base has also been updated."
-                elif kb_result["status"] == "not_indexed":
-                    kb_message = " This issue will be added to your knowledge base in the next scheduled sync."
-                else:
-                    logger.warning(
-                        f"KB update failed for issue {final_issue_id}: {kb_result.get('message')}"
-                    )
-                    kb_message = " Your knowledge base will be updated in the next scheduled sync."
-            else:
-                kb_message = ""
 
-            identifier = updated_issue.get("identifier")
-            default_msg = f"Issue {identifier} updated successfully."
-            return {
-                "status": "success",
-                "identifier": identifier,
-                "url": updated_issue.get("url"),
-                "message": f"{updated_issue.get('message', default_msg)}{kb_message}",
-            }
+                if result.rejected:
+                    logger.info("Linear issue update rejected by user")
+                    return {
+                        "status": "rejected",
+                        "message": "User declined. Do not retry or suggest alternatives.",
+                    }
+
+                final_issue_id = result.params.get("issue_id", issue_id)
+                final_document_id = result.params.get("document_id", document_id)
+                final_new_title = result.params.get("new_title", new_title)
+                final_new_description = result.params.get(
+                    "new_description", new_description
+                )
+                final_new_state_id = result.params.get("new_state_id", new_state_id)
+                final_new_assignee_id = result.params.get(
+                    "new_assignee_id", new_assignee_id
+                )
+                final_new_priority = result.params.get("new_priority", new_priority)
+                final_new_label_ids: list[str] | None = result.params.get(
+                    "new_label_ids", new_label_ids
+                )
+                final_connector_id = result.params.get(
+                    "connector_id", connector_id_from_context
+                )
+
+                if not final_connector_id:
+                    logger.error("No connector found for this issue")
+                    return {
+                        "status": "error",
+                        "message": "No connector found for this issue.",
+                    }
+
+                from sqlalchemy.future import select
+
+                from app.db import SearchSourceConnector, SearchSourceConnectorType
+
+                result = await db_session.execute(
+                    select(SearchSourceConnector).filter(
+                        SearchSourceConnector.id == final_connector_id,
+                        SearchSourceConnector.search_space_id == search_space_id,
+                        SearchSourceConnector.user_id == user_id,
+                        SearchSourceConnector.connector_type
+                        == SearchSourceConnectorType.LINEAR_CONNECTOR,
+                    )
+                )
+                connector = result.scalars().first()
+                if not connector:
+                    logger.error(
+                        f"Invalid connector_id={final_connector_id} for search_space_id={search_space_id}"
+                    )
+                    return {
+                        "status": "error",
+                        "message": "Selected Linear connector is invalid or has been disconnected.",
+                    }
+                logger.info(f"Validated Linear connector: id={final_connector_id}")
+
+                logger.info(
+                    f"Updating Linear issue with final params: issue_id={final_issue_id}"
+                )
+                linear_client = LinearConnector(
+                    session=db_session, connector_id=final_connector_id
+                )
+                updated_issue = await linear_client.update_issue(
+                    issue_id=final_issue_id,
+                    title=final_new_title,
+                    description=final_new_description,
+                    state_id=final_new_state_id,
+                    assignee_id=final_new_assignee_id,
+                    priority=final_new_priority,
+                    label_ids=final_new_label_ids,
+                )
+
+                if updated_issue.get("status") == "error":
+                    logger.error(
+                        f"Failed to update Linear issue: {updated_issue.get('message')}"
+                    )
+                    return {
+                        "status": "error",
+                        "message": updated_issue.get("message"),
+                    }
+
+                logger.info(
+                    f"update_issue result: {updated_issue.get('identifier')} - {updated_issue.get('title')}"
+                )
+
+                if final_document_id is not None:
+                    logger.info(
+                        f"Updating knowledge base for document {final_document_id}..."
+                    )
+                    kb_service = LinearKBSyncService(db_session)
+                    kb_result = await kb_service.sync_after_update(
+                        document_id=final_document_id,
+                        issue_id=final_issue_id,
+                        user_id=user_id,
+                        search_space_id=search_space_id,
+                    )
+                    if kb_result["status"] == "success":
+                        logger.info(
+                            f"Knowledge base successfully updated for issue {final_issue_id}"
+                        )
+                        kb_message = " Your knowledge base has also been updated."
+                    elif kb_result["status"] == "not_indexed":
+                        kb_message = " This issue will be added to your knowledge base in the next scheduled sync."
+                    else:
+                        logger.warning(
+                            f"KB update failed for issue {final_issue_id}: {kb_result.get('message')}"
+                        )
+                        kb_message = " Your knowledge base will be updated in the next scheduled sync."
+                else:
+                    kb_message = ""
+
+                identifier = updated_issue.get("identifier")
+                default_msg = f"Issue {identifier} updated successfully."
+                return {
+                    "status": "success",
+                    "identifier": identifier,
+                    "url": updated_issue.get("url"),
+                    "message": f"{updated_issue.get('message', default_msg)}{kb_message}",
+                }
 
         except Exception as e:
             from langgraph.errors import GraphInterrupt

surfsense_backend/app/agents/new_chat/tools/luma/create_event.py

@@ -6,6 +6,7 @@ from langchain_core.tools import tool
 from sqlalchemy.ext.asyncio import AsyncSession
 
 from app.agents.new_chat.tools.hitl import request_approval
+from app.db import async_session_maker
 
 from ._auth import LUMA_API, get_api_key, get_luma_connector, luma_headers
 
@@ -17,6 +18,23 @@ def create_create_luma_event_tool(
     search_space_id: int | None = None,
     user_id: str | None = None,
 ):
+    """
+    Factory function to create the create_luma_event tool.
+
+    The tool acquires its own short-lived ``AsyncSession`` per call via
+    :data:`async_session_maker` so the closure is safe to share across
+    HTTP requests by the compiled-agent cache. Capturing a per-request
+    session here would surface stale/closed sessions on cache hits.
+
+    Args:
+        db_session: Reserved for registry compatibility. Per-call sessions
+            are opened via :data:`async_session_maker` inside the tool body.
+
+    Returns:
+        Configured create_luma_event tool
+    """
+    del db_session  # per-call session — see docstring
+
     @tool
     async def create_luma_event(
         name: str,
@@ -40,83 +58,86 @@ def create_create_luma_event_tool(
             IMPORTANT:
             - If status is "rejected", the user explicitly declined. Do NOT retry.
         """
-        if db_session is None or search_space_id is None or user_id is None:
+        if search_space_id is None or user_id is None:
             return {"status": "error", "message": "Luma tool not properly configured."}
 
         try:
-            connector = await get_luma_connector(db_session, search_space_id, user_id)
-            if not connector:
-                return {"status": "error", "message": "No Luma connector found."}
+            async with async_session_maker() as db_session:
+                connector = await get_luma_connector(
+                    db_session, search_space_id, user_id
+                )
+                if not connector:
+                    return {"status": "error", "message": "No Luma connector found."}
 
-            result = request_approval(
-                action_type="luma_create_event",
-                tool_name="create_luma_event",
-                params={
-                    "name": name,
-                    "start_at": start_at,
-                    "end_at": end_at,
-                    "description": description,
-                    "timezone": timezone,
-                },
-                context={"connector_id": connector.id},
-            )
-
-            if result.rejected:
-                return {
-                    "status": "rejected",
-                    "message": "User declined. Event was not created.",
-                }
-
-            final_name = result.params.get("name", name)
-            final_start = result.params.get("start_at", start_at)
-            final_end = result.params.get("end_at", end_at)
-            final_desc = result.params.get("description", description)
-            final_tz = result.params.get("timezone", timezone)
-
-            api_key = get_api_key(connector)
-            headers = luma_headers(api_key)
-
-            body: dict[str, Any] = {
-                "name": final_name,
-                "start_at": final_start,
-                "end_at": final_end,
-                "timezone": final_tz,
-            }
-            if final_desc:
-                body["description_md"] = final_desc
-
-            async with httpx.AsyncClient(timeout=20.0) as client:
-                resp = await client.post(
-                    f"{LUMA_API}/event/create",
-                    headers=headers,
-                    json=body,
+                result = request_approval(
+                    action_type="luma_create_event",
+                    tool_name="create_luma_event",
+                    params={
+                        "name": name,
+                        "start_at": start_at,
+                        "end_at": end_at,
+                        "description": description,
+                        "timezone": timezone,
+                    },
+                    context={"connector_id": connector.id},
                 )
 
-            if resp.status_code == 401:
-                return {
-                    "status": "auth_error",
-                    "message": "Luma API key is invalid.",
-                    "connector_type": "luma",
-                }
-            if resp.status_code == 403:
-                return {
-                    "status": "error",
-                    "message": "Luma Plus subscription required to create events via API.",
-                }
-            if resp.status_code not in (200, 201):
-                return {
-                    "status": "error",
-                    "message": f"Luma API error: {resp.status_code} — {resp.text[:200]}",
-                }
+                if result.rejected:
+                    return {
+                        "status": "rejected",
+                        "message": "User declined. Event was not created.",
+                    }
 
-            data = resp.json()
-            event_id = data.get("api_id") or data.get("event", {}).get("api_id")
+                final_name = result.params.get("name", name)
+                final_start = result.params.get("start_at", start_at)
+                final_end = result.params.get("end_at", end_at)
+                final_desc = result.params.get("description", description)
+                final_tz = result.params.get("timezone", timezone)
 
-            return {
-                "status": "success",
-                "event_id": event_id,
-                "message": f"Event '{final_name}' created on Luma.",
-            }
+                api_key = get_api_key(connector)
+                headers = luma_headers(api_key)
+
+                body: dict[str, Any] = {
+                    "name": final_name,
+                    "start_at": final_start,
+                    "end_at": final_end,
+                    "timezone": final_tz,
+                }
+                if final_desc:
+                    body["description_md"] = final_desc
+
+                async with httpx.AsyncClient(timeout=20.0) as client:
+                    resp = await client.post(
+                        f"{LUMA_API}/event/create",
+                        headers=headers,
+                        json=body,
+                    )
+
+                if resp.status_code == 401:
+                    return {
+                        "status": "auth_error",
+                        "message": "Luma API key is invalid.",
+                        "connector_type": "luma",
+                    }
+                if resp.status_code == 403:
+                    return {
+                        "status": "error",
+                        "message": "Luma Plus subscription required to create events via API.",
+                    }
+                if resp.status_code not in (200, 201):
+                    return {
+                        "status": "error",
+                        "message": f"Luma API error: {resp.status_code} — {resp.text[:200]}",
+                    }
+
+                data = resp.json()
+                event_id = data.get("api_id") or data.get("event", {}).get("api_id")
+
+                return {
+                    "status": "success",
+                    "event_id": event_id,
+                    "message": f"Event '{final_name}' created on Luma.",
+                }
 
         except Exception as e:
             from langgraph.errors import GraphInterrupt

surfsense_backend/app/agents/new_chat/tools/luma/list_events.py

@@ -5,6 +5,8 @@ import httpx
 from langchain_core.tools import tool
 from sqlalchemy.ext.asyncio import AsyncSession
 
+from app.db import async_session_maker
+
 from ._auth import LUMA_API, get_api_key, get_luma_connector, luma_headers
 
 logger = logging.getLogger(__name__)
@@ -15,6 +17,23 @@ def create_list_luma_events_tool(
     search_space_id: int | None = None,
     user_id: str | None = None,
 ):
+    """
+    Factory function to create the list_luma_events tool.
+
+    The tool acquires its own short-lived ``AsyncSession`` per call via
+    :data:`async_session_maker` so the closure is safe to share across
+    HTTP requests by the compiled-agent cache. Capturing a per-request
+    session here would surface stale/closed sessions on cache hits.
+
+    Args:
+        db_session: Reserved for registry compatibility. Per-call sessions
+            are opened via :data:`async_session_maker` inside the tool body.
+
+    Returns:
+        Configured list_luma_events tool
+    """
+    del db_session  # per-call session — see docstring
+
     @tool
     async def list_luma_events(
         max_results: int = 25,
@@ -28,77 +47,80 @@ def create_list_luma_events_tool(
             Dictionary with status and a list of events including
             event_id, name, start_at, end_at, location, url.
         """
-        if db_session is None or search_space_id is None or user_id is None:
+        if search_space_id is None or user_id is None:
             return {"status": "error", "message": "Luma tool not properly configured."}
 
         max_results = min(max_results, 50)
 
         try:
-            connector = await get_luma_connector(db_session, search_space_id, user_id)
-            if not connector:
-                return {"status": "error", "message": "No Luma connector found."}
+            async with async_session_maker() as db_session:
+                connector = await get_luma_connector(
+                    db_session, search_space_id, user_id
+                )
+                if not connector:
+                    return {"status": "error", "message": "No Luma connector found."}
 
-            api_key = get_api_key(connector)
-            headers = luma_headers(api_key)
+                api_key = get_api_key(connector)
+                headers = luma_headers(api_key)
 
-            all_entries: list[dict] = []
-            cursor = None
+                all_entries: list[dict] = []
+                cursor = None
 
-            async with httpx.AsyncClient(timeout=20.0) as client:
-                while len(all_entries) < max_results:
-                    params: dict[str, Any] = {
-                        "limit": min(100, max_results - len(all_entries))
-                    }
-                    if cursor:
-                        params["cursor"] = cursor
+                async with httpx.AsyncClient(timeout=20.0) as client:
+                    while len(all_entries) < max_results:
+                        params: dict[str, Any] = {
+                            "limit": min(100, max_results - len(all_entries))
+                        }
+                        if cursor:
+                            params["cursor"] = cursor
 
-                    resp = await client.get(
-                        f"{LUMA_API}/calendar/list-events",
-                        headers=headers,
-                        params=params,
+                        resp = await client.get(
+                            f"{LUMA_API}/calendar/list-events",
+                            headers=headers,
+                            params=params,
+                        )
+
+                        if resp.status_code == 401:
+                            return {
+                                "status": "auth_error",
+                                "message": "Luma API key is invalid.",
+                                "connector_type": "luma",
+                            }
+                        if resp.status_code != 200:
+                            return {
+                                "status": "error",
+                                "message": f"Luma API error: {resp.status_code}",
+                            }
+
+                        data = resp.json()
+                        entries = data.get("entries", [])
+                        if not entries:
+                            break
+                        all_entries.extend(entries)
+
+                        next_cursor = data.get("next_cursor")
+                        if not next_cursor:
+                            break
+                        cursor = next_cursor
+
+                events = []
+                for entry in all_entries[:max_results]:
+                    ev = entry.get("event", {})
+                    geo = ev.get("geo_info", {})
+                    events.append(
+                        {
+                            "event_id": entry.get("api_id"),
+                            "name": ev.get("name", "Untitled"),
+                            "start_at": ev.get("start_at", ""),
+                            "end_at": ev.get("end_at", ""),
+                            "timezone": ev.get("timezone", ""),
+                            "location": geo.get("name", ""),
+                            "url": ev.get("url", ""),
+                            "visibility": ev.get("visibility", ""),
+                        }
                     )
 
-                    if resp.status_code == 401:
-                        return {
-                            "status": "auth_error",
-                            "message": "Luma API key is invalid.",
-                            "connector_type": "luma",
-                        }
-                    if resp.status_code != 200:
-                        return {
-                            "status": "error",
-                            "message": f"Luma API error: {resp.status_code}",
-                        }
-
-                    data = resp.json()
-                    entries = data.get("entries", [])
-                    if not entries:
-                        break
-                    all_entries.extend(entries)
-
-                    next_cursor = data.get("next_cursor")
-                    if not next_cursor:
-                        break
-                    cursor = next_cursor
-
-            events = []
-            for entry in all_entries[:max_results]:
-                ev = entry.get("event", {})
-                geo = ev.get("geo_info", {})
-                events.append(
-                    {
-                        "event_id": entry.get("api_id"),
-                        "name": ev.get("name", "Untitled"),
-                        "start_at": ev.get("start_at", ""),
-                        "end_at": ev.get("end_at", ""),
-                        "timezone": ev.get("timezone", ""),
-                        "location": geo.get("name", ""),
-                        "url": ev.get("url", ""),
-                        "visibility": ev.get("visibility", ""),
-                    }
-                )
-
-            return {"status": "success", "events": events, "total": len(events)}
+                return {"status": "success", "events": events, "total": len(events)}
 
         except Exception as e:
             from langgraph.errors import GraphInterrupt

surfsense_backend/app/agents/new_chat/tools/luma/read_event.py

@@ -5,6 +5,8 @@ import httpx
 from langchain_core.tools import tool
 from sqlalchemy.ext.asyncio import AsyncSession
 
+from app.db import async_session_maker
+
 from ._auth import LUMA_API, get_api_key, get_luma_connector, luma_headers
 
 logger = logging.getLogger(__name__)
@@ -15,6 +17,23 @@ def create_read_luma_event_tool(
     search_space_id: int | None = None,
     user_id: str | None = None,
 ):
+    """
+    Factory function to create the read_luma_event tool.
+
+    The tool acquires its own short-lived ``AsyncSession`` per call via
+    :data:`async_session_maker` so the closure is safe to share across
+    HTTP requests by the compiled-agent cache. Capturing a per-request
+    session here would surface stale/closed sessions on cache hits.
+
+    Args:
+        db_session: Reserved for registry compatibility. Per-call sessions
+            are opened via :data:`async_session_maker` inside the tool body.
+
+    Returns:
+        Configured read_luma_event tool
+    """
+    del db_session  # per-call session — see docstring
+
     @tool
     async def read_luma_event(event_id: str) -> dict[str, Any]:
         """Read detailed information about a specific Luma event.
@@ -26,60 +45,63 @@ def create_read_luma_event_tool(
             Dictionary with status and full event details including
             description, attendees count, meeting URL.
         """
-        if db_session is None or search_space_id is None or user_id is None:
+        if search_space_id is None or user_id is None:
             return {"status": "error", "message": "Luma tool not properly configured."}
 
         try:
-            connector = await get_luma_connector(db_session, search_space_id, user_id)
-            if not connector:
-                return {"status": "error", "message": "No Luma connector found."}
-
-            api_key = get_api_key(connector)
-            headers = luma_headers(api_key)
-
-            async with httpx.AsyncClient(timeout=15.0) as client:
-                resp = await client.get(
-                    f"{LUMA_API}/events/{event_id}",
-                    headers=headers,
+            async with async_session_maker() as db_session:
+                connector = await get_luma_connector(
+                    db_session, search_space_id, user_id
                 )
+                if not connector:
+                    return {"status": "error", "message": "No Luma connector found."}
 
-            if resp.status_code == 401:
-                return {
-                    "status": "auth_error",
-                    "message": "Luma API key is invalid.",
-                    "connector_type": "luma",
-                }
-            if resp.status_code == 404:
-                return {
-                    "status": "not_found",
-                    "message": f"Event '{event_id}' not found.",
-                }
-            if resp.status_code != 200:
-                return {
-                    "status": "error",
-                    "message": f"Luma API error: {resp.status_code}",
+                api_key = get_api_key(connector)
+                headers = luma_headers(api_key)
+
+                async with httpx.AsyncClient(timeout=15.0) as client:
+                    resp = await client.get(
+                        f"{LUMA_API}/events/{event_id}",
+                        headers=headers,
+                    )
+
+                if resp.status_code == 401:
+                    return {
+                        "status": "auth_error",
+                        "message": "Luma API key is invalid.",
+                        "connector_type": "luma",
+                    }
+                if resp.status_code == 404:
+                    return {
+                        "status": "not_found",
+                        "message": f"Event '{event_id}' not found.",
+                    }
+                if resp.status_code != 200:
+                    return {
+                        "status": "error",
+                        "message": f"Luma API error: {resp.status_code}",
+                    }
+
+                data = resp.json()
+                ev = data.get("event", data)
+                geo = ev.get("geo_info", {})
+
+                event_detail = {
+                    "event_id": event_id,
+                    "name": ev.get("name", ""),
+                    "description": ev.get("description", ""),
+                    "start_at": ev.get("start_at", ""),
+                    "end_at": ev.get("end_at", ""),
+                    "timezone": ev.get("timezone", ""),
+                    "location_name": geo.get("name", ""),
+                    "address": geo.get("address", ""),
+                    "url": ev.get("url", ""),
+                    "meeting_url": ev.get("meeting_url", ""),
+                    "visibility": ev.get("visibility", ""),
+                    "cover_url": ev.get("cover_url", ""),
                 }
 
-            data = resp.json()
-            ev = data.get("event", data)
-            geo = ev.get("geo_info", {})
-
-            event_detail = {
-                "event_id": event_id,
-                "name": ev.get("name", ""),
-                "description": ev.get("description", ""),
-                "start_at": ev.get("start_at", ""),
-                "end_at": ev.get("end_at", ""),
-                "timezone": ev.get("timezone", ""),
-                "location_name": geo.get("name", ""),
-                "address": geo.get("address", ""),
-                "url": ev.get("url", ""),
-                "meeting_url": ev.get("meeting_url", ""),
-                "visibility": ev.get("visibility", ""),
-                "cover_url": ev.get("cover_url", ""),
-            }
-
-            return {"status": "success", "event": event_detail}
+                return {"status": "success", "event": event_detail}
 
         except Exception as e:
             from langgraph.errors import GraphInterrupt

surfsense_backend/app/agents/new_chat/tools/notion/create_page.py

@@ -6,6 +6,7 @@ from sqlalchemy.ext.asyncio import AsyncSession
 
 from app.agents.new_chat.tools.hitl import request_approval
 from app.connectors.notion_history import NotionAPIError, NotionHistoryConnector
+from app.db import async_session_maker
 from app.services.notion import NotionToolMetadataService
 
 logger = logging.getLogger(__name__)
@@ -20,8 +21,17 @@ def create_create_notion_page_tool(
     """
     Factory function to create the create_notion_page tool.
 
+    The tool acquires its own short-lived ``AsyncSession`` per call via
+    :data:`async_session_maker`. This is critical for the compiled-agent
+    cache: the compiled graph (and therefore this closure) is reused
+    across HTTP requests, so capturing a per-request session here would
+    surface stale/closed sessions on cache hits. Per-call sessions also
+    keep the request's outer transaction free of long-running Notion API
+    blocking.
+
     Args:
-        db_session: Database session for accessing Notion connector
+        db_session: Reserved for registry compatibility. Per-call sessions
+            are opened via :data:`async_session_maker` inside the tool body.
         search_space_id: Search space ID to find the Notion connector
         user_id: User ID for fetching user-specific context
         connector_id: Optional specific connector ID (if known)
@@ -29,6 +39,7 @@ def create_create_notion_page_tool(
     Returns:
         Configured create_notion_page tool
     """
+    del db_session  # per-call session — see docstring
 
     @tool
     async def create_notion_page(
@@ -67,7 +78,7 @@ def create_create_notion_page_tool(
         """
         logger.info(f"create_notion_page called: title='{title}'")
 
-        if db_session is None or search_space_id is None or user_id is None:
+        if search_space_id is None or user_id is None:
             logger.error(
                 "Notion tool not properly configured - missing required parameters"
             )
@@ -77,154 +88,157 @@ def create_create_notion_page_tool(
             }
 
         try:
-            metadata_service = NotionToolMetadataService(db_session)
-            context = await metadata_service.get_creation_context(
-                search_space_id, user_id
-            )
-
-            if "error" in context:
-                logger.error(f"Failed to fetch creation context: {context['error']}")
-                return {
-                    "status": "error",
-                    "message": context["error"],
-                }
-
-            accounts = context.get("accounts", [])
-            if accounts and all(a.get("auth_expired") for a in accounts):
-                logger.warning("All Notion accounts have expired authentication")
-                return {
-                    "status": "auth_error",
-                    "message": "All connected Notion accounts need re-authentication. Please re-authenticate in your connector settings.",
-                    "connector_type": "notion",
-                }
-
-            logger.info(f"Requesting approval for creating Notion page: '{title}'")
-            result = request_approval(
-                action_type="notion_page_creation",
-                tool_name="create_notion_page",
-                params={
-                    "title": title,
-                    "content": content,
-                    "parent_page_id": None,
-                    "connector_id": connector_id,
-                },
-                context=context,
-            )
-
-            if result.rejected:
-                logger.info("Notion page creation rejected by user")
-                return {
-                    "status": "rejected",
-                    "message": "User declined. Do not retry or suggest alternatives.",
-                }
-
-            final_title = result.params.get("title", title)
-            final_content = result.params.get("content", content)
-            final_parent_page_id = result.params.get("parent_page_id")
-            final_connector_id = result.params.get("connector_id", connector_id)
-
-            if not final_title or not final_title.strip():
-                logger.error("Title is empty or contains only whitespace")
-                return {
-                    "status": "error",
-                    "message": "Page title cannot be empty. Please provide a valid title.",
-                }
-
-            logger.info(
-                f"Creating Notion page with final params: title='{final_title}'"
-            )
-
-            from sqlalchemy.future import select
-
-            from app.db import SearchSourceConnector, SearchSourceConnectorType
-
-            actual_connector_id = final_connector_id
-            if actual_connector_id is None:
-                result = await db_session.execute(
-                    select(SearchSourceConnector).filter(
-                        SearchSourceConnector.search_space_id == search_space_id,
-                        SearchSourceConnector.user_id == user_id,
-                        SearchSourceConnector.connector_type
-                        == SearchSourceConnectorType.NOTION_CONNECTOR,
-                    )
+            async with async_session_maker() as db_session:
+                metadata_service = NotionToolMetadataService(db_session)
+                context = await metadata_service.get_creation_context(
+                    search_space_id, user_id
                 )
-                connector = result.scalars().first()
 
-                if not connector:
-                    logger.warning(
-                        f"No Notion connector found for search_space_id={search_space_id}"
-                    )
-                    return {
-                        "status": "error",
-                        "message": "No Notion connector found. Please connect Notion in your workspace settings.",
-                    }
-
-                actual_connector_id = connector.id
-                logger.info(f"Found Notion connector: id={actual_connector_id}")
-            else:
-                result = await db_session.execute(
-                    select(SearchSourceConnector).filter(
-                        SearchSourceConnector.id == actual_connector_id,
-                        SearchSourceConnector.search_space_id == search_space_id,
-                        SearchSourceConnector.user_id == user_id,
-                        SearchSourceConnector.connector_type
-                        == SearchSourceConnectorType.NOTION_CONNECTOR,
-                    )
-                )
-                connector = result.scalars().first()
-
-                if not connector:
+                if "error" in context:
                     logger.error(
-                        f"Invalid connector_id={actual_connector_id} for search_space_id={search_space_id}"
+                        f"Failed to fetch creation context: {context['error']}"
                     )
                     return {
                         "status": "error",
-                        "message": "Selected Notion account is invalid or has been disconnected. Please select a valid account.",
+                        "message": context["error"],
                     }
-                logger.info(f"Validated Notion connector: id={actual_connector_id}")
 
-            notion_connector = NotionHistoryConnector(
-                session=db_session,
-                connector_id=actual_connector_id,
-            )
+                accounts = context.get("accounts", [])
+                if accounts and all(a.get("auth_expired") for a in accounts):
+                    logger.warning("All Notion accounts have expired authentication")
+                    return {
+                        "status": "auth_error",
+                        "message": "All connected Notion accounts need re-authentication. Please re-authenticate in your connector settings.",
+                        "connector_type": "notion",
+                    }
 
-            result = await notion_connector.create_page(
-                title=final_title,
-                content=final_content,
-                parent_page_id=final_parent_page_id,
-            )
-            logger.info(
-                f"create_page result: {result.get('status')} - {result.get('message', '')}"
-            )
+                logger.info(f"Requesting approval for creating Notion page: '{title}'")
+                result = request_approval(
+                    action_type="notion_page_creation",
+                    tool_name="create_notion_page",
+                    params={
+                        "title": title,
+                        "content": content,
+                        "parent_page_id": None,
+                        "connector_id": connector_id,
+                    },
+                    context=context,
+                )
 
-            if result.get("status") == "success":
-                kb_message_suffix = ""
-                try:
-                    from app.services.notion import NotionKBSyncService
+                if result.rejected:
+                    logger.info("Notion page creation rejected by user")
+                    return {
+                        "status": "rejected",
+                        "message": "User declined. Do not retry or suggest alternatives.",
+                    }
 
-                    kb_service = NotionKBSyncService(db_session)
-                    kb_result = await kb_service.sync_after_create(
-                        page_id=result.get("page_id"),
-                        page_title=result.get("title", final_title),
-                        page_url=result.get("url"),
-                        content=final_content,
-                        connector_id=actual_connector_id,
-                        search_space_id=search_space_id,
-                        user_id=user_id,
-                    )
-                    if kb_result["status"] == "success":
-                        kb_message_suffix = (
-                            " Your knowledge base has also been updated."
+                final_title = result.params.get("title", title)
+                final_content = result.params.get("content", content)
+                final_parent_page_id = result.params.get("parent_page_id")
+                final_connector_id = result.params.get("connector_id", connector_id)
+
+                if not final_title or not final_title.strip():
+                    logger.error("Title is empty or contains only whitespace")
+                    return {
+                        "status": "error",
+                        "message": "Page title cannot be empty. Please provide a valid title.",
+                    }
+
+                logger.info(
+                    f"Creating Notion page with final params: title='{final_title}'"
+                )
+
+                from sqlalchemy.future import select
+
+                from app.db import SearchSourceConnector, SearchSourceConnectorType
+
+                actual_connector_id = final_connector_id
+                if actual_connector_id is None:
+                    result = await db_session.execute(
+                        select(SearchSourceConnector).filter(
+                            SearchSourceConnector.search_space_id == search_space_id,
+                            SearchSourceConnector.user_id == user_id,
+                            SearchSourceConnector.connector_type
+                            == SearchSourceConnectorType.NOTION_CONNECTOR,
                         )
-                    else:
+                    )
+                    connector = result.scalars().first()
+
+                    if not connector:
+                        logger.warning(
+                            f"No Notion connector found for search_space_id={search_space_id}"
+                        )
+                        return {
+                            "status": "error",
+                            "message": "No Notion connector found. Please connect Notion in your workspace settings.",
+                        }
+
+                    actual_connector_id = connector.id
+                    logger.info(f"Found Notion connector: id={actual_connector_id}")
+                else:
+                    result = await db_session.execute(
+                        select(SearchSourceConnector).filter(
+                            SearchSourceConnector.id == actual_connector_id,
+                            SearchSourceConnector.search_space_id == search_space_id,
+                            SearchSourceConnector.user_id == user_id,
+                            SearchSourceConnector.connector_type
+                            == SearchSourceConnectorType.NOTION_CONNECTOR,
+                        )
+                    )
+                    connector = result.scalars().first()
+
+                    if not connector:
+                        logger.error(
+                            f"Invalid connector_id={actual_connector_id} for search_space_id={search_space_id}"
+                        )
+                        return {
+                            "status": "error",
+                            "message": "Selected Notion account is invalid or has been disconnected. Please select a valid account.",
+                        }
+                    logger.info(f"Validated Notion connector: id={actual_connector_id}")
+
+                notion_connector = NotionHistoryConnector(
+                    session=db_session,
+                    connector_id=actual_connector_id,
+                )
+
+                result = await notion_connector.create_page(
+                    title=final_title,
+                    content=final_content,
+                    parent_page_id=final_parent_page_id,
+                )
+                logger.info(
+                    f"create_page result: {result.get('status')} - {result.get('message', '')}"
+                )
+
+                if result.get("status") == "success":
+                    kb_message_suffix = ""
+                    try:
+                        from app.services.notion import NotionKBSyncService
+
+                        kb_service = NotionKBSyncService(db_session)
+                        kb_result = await kb_service.sync_after_create(
+                            page_id=result.get("page_id"),
+                            page_title=result.get("title", final_title),
+                            page_url=result.get("url"),
+                            content=final_content,
+                            connector_id=actual_connector_id,
+                            search_space_id=search_space_id,
+                            user_id=user_id,
+                        )
+                        if kb_result["status"] == "success":
+                            kb_message_suffix = (
+                                " Your knowledge base has also been updated."
+                            )
+                        else:
+                            kb_message_suffix = " This page will be added to your knowledge base in the next scheduled sync."
+                    except Exception as kb_err:
+                        logger.warning(f"KB sync after create failed: {kb_err}")
                         kb_message_suffix = " This page will be added to your knowledge base in the next scheduled sync."
-                except Exception as kb_err:
-                    logger.warning(f"KB sync after create failed: {kb_err}")
-                    kb_message_suffix = " This page will be added to your knowledge base in the next scheduled sync."
 
-                result["message"] = result.get("message", "") + kb_message_suffix
+                    result["message"] = result.get("message", "") + kb_message_suffix
 
-            return result
+                return result
 
         except Exception as e:
             from langgraph.errors import GraphInterrupt

surfsense_backend/app/agents/new_chat/tools/notion/delete_page.py

@@ -6,6 +6,7 @@ from sqlalchemy.ext.asyncio import AsyncSession
 
 from app.agents.new_chat.tools.hitl import request_approval
 from app.connectors.notion_history import NotionAPIError, NotionHistoryConnector
+from app.db import async_session_maker
 from app.services.notion.tool_metadata_service import NotionToolMetadataService
 
 logger = logging.getLogger(__name__)
@@ -20,8 +21,14 @@ def create_delete_notion_page_tool(
     """
     Factory function to create the delete_notion_page tool.
 
+    The tool acquires its own short-lived ``AsyncSession`` per call via
+    :data:`async_session_maker` so the closure is safe to share across
+    HTTP requests by the compiled-agent cache. Capturing a per-request
+    session here would surface stale/closed sessions on cache hits.
+
     Args:
-        db_session: Database session for accessing Notion connector
+        db_session: Reserved for registry compatibility. Per-call sessions
+            are opened via :data:`async_session_maker` inside the tool body.
         search_space_id: Search space ID to find the Notion connector
         user_id: User ID for finding the correct Notion connector
         connector_id: Optional specific connector ID (if known)
@@ -29,6 +36,7 @@ def create_delete_notion_page_tool(
     Returns:
         Configured delete_notion_page tool
     """
+    del db_session  # per-call session — see docstring
 
     @tool
     async def delete_notion_page(
@@ -63,7 +71,7 @@ def create_delete_notion_page_tool(
             f"delete_notion_page called: page_title='{page_title}', delete_from_kb={delete_from_kb}"
         )
 
-        if db_session is None or search_space_id is None or user_id is None:
+        if search_space_id is None or user_id is None:
             logger.error(
                 "Notion tool not properly configured - missing required parameters"
             )
@@ -73,164 +81,167 @@ def create_delete_notion_page_tool(
             }
 
         try:
-            # Get page context (page_id, account, title) from indexed data
-            metadata_service = NotionToolMetadataService(db_session)
-            context = await metadata_service.get_delete_context(
-                search_space_id, user_id, page_title
-            )
-
-            if "error" in context:
-                error_msg = context["error"]
-                # Check if it's a "not found" error (softer handling for LLM)
-                if "not found" in error_msg.lower():
-                    logger.warning(f"Page not found: {error_msg}")
-                    return {
-                        "status": "not_found",
-                        "message": error_msg,
-                    }
-                else:
-                    logger.error(f"Failed to fetch delete context: {error_msg}")
-                    return {
-                        "status": "error",
-                        "message": error_msg,
-                    }
-
-            account = context.get("account", {})
-            if account.get("auth_expired"):
-                logger.warning(
-                    "Notion account %s has expired authentication",
-                    account.get("id"),
+            async with async_session_maker() as db_session:
+                # Get page context (page_id, account, title) from indexed data
+                metadata_service = NotionToolMetadataService(db_session)
+                context = await metadata_service.get_delete_context(
+                    search_space_id, user_id, page_title
                 )
-                return {
-                    "status": "auth_error",
-                    "message": "The Notion account for this page needs re-authentication. Please re-authenticate in your connector settings.",
-                }
 
-            page_id = context.get("page_id")
-            connector_id_from_context = account.get("id")
-            document_id = context.get("document_id")
-
-            logger.info(
-                f"Requesting approval for deleting Notion page: '{page_title}' (page_id={page_id}, delete_from_kb={delete_from_kb})"
-            )
-
-            result = request_approval(
-                action_type="notion_page_deletion",
-                tool_name="delete_notion_page",
-                params={
-                    "page_id": page_id,
-                    "connector_id": connector_id_from_context,
-                    "delete_from_kb": delete_from_kb,
-                },
-                context=context,
-            )
-
-            if result.rejected:
-                logger.info("Notion page deletion rejected by user")
-                return {
-                    "status": "rejected",
-                    "message": "User declined. Do not retry or suggest alternatives.",
-                }
-
-            final_page_id = result.params.get("page_id", page_id)
-            final_connector_id = result.params.get(
-                "connector_id", connector_id_from_context
-            )
-            final_delete_from_kb = result.params.get("delete_from_kb", delete_from_kb)
-
-            logger.info(
-                f"Deleting Notion page with final params: page_id={final_page_id}, connector_id={final_connector_id}, delete_from_kb={final_delete_from_kb}"
-            )
-
-            from sqlalchemy.future import select
-
-            from app.db import SearchSourceConnector, SearchSourceConnectorType
-
-            # Validate the connector
-            if final_connector_id:
-                result = await db_session.execute(
-                    select(SearchSourceConnector).filter(
-                        SearchSourceConnector.id == final_connector_id,
-                        SearchSourceConnector.search_space_id == search_space_id,
-                        SearchSourceConnector.user_id == user_id,
-                        SearchSourceConnector.connector_type
-                        == SearchSourceConnectorType.NOTION_CONNECTOR,
-                    )
-                )
-                connector = result.scalars().first()
-
-                if not connector:
-                    logger.error(
-                        f"Invalid connector_id={final_connector_id} for search_space_id={search_space_id}"
-                    )
-                    return {
-                        "status": "error",
-                        "message": "Selected Notion account is invalid or has been disconnected. Please select a valid account.",
-                    }
-                actual_connector_id = connector.id
-                logger.info(f"Validated Notion connector: id={actual_connector_id}")
-            else:
-                logger.error("No connector found for this page")
-                return {
-                    "status": "error",
-                    "message": "No connector found for this page.",
-                }
-
-            # Create connector instance
-            notion_connector = NotionHistoryConnector(
-                session=db_session,
-                connector_id=actual_connector_id,
-            )
-
-            # Delete the page from Notion
-            result = await notion_connector.delete_page(page_id=final_page_id)
-            logger.info(
-                f"delete_page result: {result.get('status')} - {result.get('message', '')}"
-            )
-
-            # If deletion was successful and user wants to delete from KB
-            deleted_from_kb = False
-            if (
-                result.get("status") == "success"
-                and final_delete_from_kb
-                and document_id
-            ):
-                try:
-                    from sqlalchemy.future import select
-
-                    from app.db import Document
-
-                    # Get the document
-                    doc_result = await db_session.execute(
-                        select(Document).filter(Document.id == document_id)
-                    )
-                    document = doc_result.scalars().first()
-
-                    if document:
-                        await db_session.delete(document)
-                        await db_session.commit()
-                        deleted_from_kb = True
-                        logger.info(
-                            f"Deleted document {document_id} from knowledge base"
-                        )
+                if "error" in context:
+                    error_msg = context["error"]
+                    # Check if it's a "not found" error (softer handling for LLM)
+                    if "not found" in error_msg.lower():
+                        logger.warning(f"Page not found: {error_msg}")
+                        return {
+                            "status": "not_found",
+                            "message": error_msg,
+                        }
                     else:
-                        logger.warning(f"Document {document_id} not found in KB")
-                except Exception as e:
-                    logger.error(f"Failed to delete document from KB: {e}")
-                    await db_session.rollback()
-                    result["warning"] = (
-                        f"Page deleted from Notion, but failed to remove from knowledge base: {e!s}"
-                    )
+                        logger.error(f"Failed to fetch delete context: {error_msg}")
+                        return {
+                            "status": "error",
+                            "message": error_msg,
+                        }
 
-            # Update result with KB deletion status
-            if result.get("status") == "success":
-                result["deleted_from_kb"] = deleted_from_kb
-                if deleted_from_kb:
-                    result["message"] = (
-                        f"{result.get('message', '')} (also removed from knowledge base)"
+                account = context.get("account", {})
+                if account.get("auth_expired"):
+                    logger.warning(
+                        "Notion account %s has expired authentication",
+                        account.get("id"),
                     )
+                    return {
+                        "status": "auth_error",
+                        "message": "The Notion account for this page needs re-authentication. Please re-authenticate in your connector settings.",
+                    }
 
-            return result
+                page_id = context.get("page_id")
+                connector_id_from_context = account.get("id")
+                document_id = context.get("document_id")
+
+                logger.info(
+                    f"Requesting approval for deleting Notion page: '{page_title}' (page_id={page_id}, delete_from_kb={delete_from_kb})"
+                )
+
+                result = request_approval(
+                    action_type="notion_page_deletion",
+                    tool_name="delete_notion_page",
+                    params={
+                        "page_id": page_id,
+                        "connector_id": connector_id_from_context,
+                        "delete_from_kb": delete_from_kb,
+                    },
+                    context=context,
+                )
+
+                if result.rejected:
+                    logger.info("Notion page deletion rejected by user")
+                    return {
+                        "status": "rejected",
+                        "message": "User declined. Do not retry or suggest alternatives.",
+                    }
+
+                final_page_id = result.params.get("page_id", page_id)
+                final_connector_id = result.params.get(
+                    "connector_id", connector_id_from_context
+                )
+                final_delete_from_kb = result.params.get(
+                    "delete_from_kb", delete_from_kb
+                )
+
+                logger.info(
+                    f"Deleting Notion page with final params: page_id={final_page_id}, connector_id={final_connector_id}, delete_from_kb={final_delete_from_kb}"
+                )
+
+                from sqlalchemy.future import select
+
+                from app.db import SearchSourceConnector, SearchSourceConnectorType
+
+                # Validate the connector
+                if final_connector_id:
+                    result = await db_session.execute(
+                        select(SearchSourceConnector).filter(
+                            SearchSourceConnector.id == final_connector_id,
+                            SearchSourceConnector.search_space_id == search_space_id,
+                            SearchSourceConnector.user_id == user_id,
+                            SearchSourceConnector.connector_type
+                            == SearchSourceConnectorType.NOTION_CONNECTOR,
+                        )
+                    )
+                    connector = result.scalars().first()
+
+                    if not connector:
+                        logger.error(
+                            f"Invalid connector_id={final_connector_id} for search_space_id={search_space_id}"
+                        )
+                        return {
+                            "status": "error",
+                            "message": "Selected Notion account is invalid or has been disconnected. Please select a valid account.",
+                        }
+                    actual_connector_id = connector.id
+                    logger.info(f"Validated Notion connector: id={actual_connector_id}")
+                else:
+                    logger.error("No connector found for this page")
+                    return {
+                        "status": "error",
+                        "message": "No connector found for this page.",
+                    }
+
+                # Create connector instance
+                notion_connector = NotionHistoryConnector(
+                    session=db_session,
+                    connector_id=actual_connector_id,
+                )
+
+                # Delete the page from Notion
+                result = await notion_connector.delete_page(page_id=final_page_id)
+                logger.info(
+                    f"delete_page result: {result.get('status')} - {result.get('message', '')}"
+                )
+
+                # If deletion was successful and user wants to delete from KB
+                deleted_from_kb = False
+                if (
+                    result.get("status") == "success"
+                    and final_delete_from_kb
+                    and document_id
+                ):
+                    try:
+                        from sqlalchemy.future import select
+
+                        from app.db import Document
+
+                        # Get the document
+                        doc_result = await db_session.execute(
+                            select(Document).filter(Document.id == document_id)
+                        )
+                        document = doc_result.scalars().first()
+
+                        if document:
+                            await db_session.delete(document)
+                            await db_session.commit()
+                            deleted_from_kb = True
+                            logger.info(
+                                f"Deleted document {document_id} from knowledge base"
+                            )
+                        else:
+                            logger.warning(f"Document {document_id} not found in KB")
+                    except Exception as e:
+                        logger.error(f"Failed to delete document from KB: {e}")
+                        await db_session.rollback()
+                        result["warning"] = (
+                            f"Page deleted from Notion, but failed to remove from knowledge base: {e!s}"
+                        )
+
+                # Update result with KB deletion status
+                if result.get("status") == "success":
+                    result["deleted_from_kb"] = deleted_from_kb
+                    if deleted_from_kb:
+                        result["message"] = (
+                            f"{result.get('message', '')} (also removed from knowledge base)"
+                        )
+
+                return result
 
         except Exception as e:
             from langgraph.errors import GraphInterrupt

surfsense_backend/app/agents/new_chat/tools/notion/update_page.py

@@ -6,6 +6,7 @@ from sqlalchemy.ext.asyncio import AsyncSession
 
 from app.agents.new_chat.tools.hitl import request_approval
 from app.connectors.notion_history import NotionAPIError, NotionHistoryConnector
+from app.db import async_session_maker
 from app.services.notion import NotionToolMetadataService
 
 logger = logging.getLogger(__name__)
@@ -20,8 +21,14 @@ def create_update_notion_page_tool(
     """
     Factory function to create the update_notion_page tool.
 
+    The tool acquires its own short-lived ``AsyncSession`` per call via
+    :data:`async_session_maker` so the closure is safe to share across
+    HTTP requests by the compiled-agent cache (see
+    ``create_create_notion_page_tool`` for the full rationale).
+
     Args:
-        db_session: Database session for accessing Notion connector
+        db_session: Reserved for registry compatibility. Per-call sessions
+            are opened via :data:`async_session_maker` inside the tool body.
         search_space_id: Search space ID to find the Notion connector
         user_id: User ID for fetching user-specific context
         connector_id: Optional specific connector ID (if known)
@@ -29,6 +36,7 @@ def create_update_notion_page_tool(
     Returns:
         Configured update_notion_page tool
     """
+    del db_session  # per-call session — see docstring
 
     @tool
     async def update_notion_page(
@@ -71,7 +79,7 @@ def create_update_notion_page_tool(
             f"update_notion_page called: page_title='{page_title}', content_length={len(content) if content else 0}"
         )
 
-        if db_session is None or search_space_id is None or user_id is None:
+        if search_space_id is None or user_id is None:
             logger.error(
                 "Notion tool not properly configured - missing required parameters"
             )
@@ -88,152 +96,155 @@ def create_update_notion_page_tool(
             }
 
         try:
-            metadata_service = NotionToolMetadataService(db_session)
-            context = await metadata_service.get_update_context(
-                search_space_id, user_id, page_title
-            )
-
-            if "error" in context:
-                error_msg = context["error"]
-                # Check if it's a "not found" error (softer handling for LLM)
-                if "not found" in error_msg.lower():
-                    logger.warning(f"Page not found: {error_msg}")
-                    return {
-                        "status": "not_found",
-                        "message": error_msg,
-                    }
-                else:
-                    logger.error(f"Failed to fetch update context: {error_msg}")
-                    return {
-                        "status": "error",
-                        "message": error_msg,
-                    }
-
-            account = context.get("account", {})
-            if account.get("auth_expired"):
-                logger.warning(
-                    "Notion account %s has expired authentication",
-                    account.get("id"),
-                )
-                return {
-                    "status": "auth_error",
-                    "message": "The Notion account for this page needs re-authentication. Please re-authenticate in your connector settings.",
-                }
-
-            page_id = context.get("page_id")
-            document_id = context.get("document_id")
-            connector_id_from_context = context.get("account", {}).get("id")
-
-            logger.info(
-                f"Requesting approval for updating Notion page: '{page_title}' (page_id={page_id})"
-            )
-            result = request_approval(
-                action_type="notion_page_update",
-                tool_name="update_notion_page",
-                params={
-                    "page_id": page_id,
-                    "content": content,
-                    "connector_id": connector_id_from_context,
-                },
-                context=context,
-            )
-
-            if result.rejected:
-                logger.info("Notion page update rejected by user")
-                return {
-                    "status": "rejected",
-                    "message": "User declined. Do not retry or suggest alternatives.",
-                }
-
-            final_page_id = result.params.get("page_id", page_id)
-            final_content = result.params.get("content", content)
-            final_connector_id = result.params.get(
-                "connector_id", connector_id_from_context
-            )
-
-            logger.info(
-                f"Updating Notion page with final params: page_id={final_page_id}, has_content={final_content is not None}"
-            )
-
-            from sqlalchemy.future import select
-
-            from app.db import SearchSourceConnector, SearchSourceConnectorType
-
-            if final_connector_id:
-                result = await db_session.execute(
-                    select(SearchSourceConnector).filter(
-                        SearchSourceConnector.id == final_connector_id,
-                        SearchSourceConnector.search_space_id == search_space_id,
-                        SearchSourceConnector.user_id == user_id,
-                        SearchSourceConnector.connector_type
-                        == SearchSourceConnectorType.NOTION_CONNECTOR,
-                    )
-                )
-                connector = result.scalars().first()
-
-                if not connector:
-                    logger.error(
-                        f"Invalid connector_id={final_connector_id} for search_space_id={search_space_id}"
-                    )
-                    return {
-                        "status": "error",
-                        "message": "Selected Notion account is invalid or has been disconnected. Please select a valid account.",
-                    }
-                actual_connector_id = connector.id
-                logger.info(f"Validated Notion connector: id={actual_connector_id}")
-            else:
-                logger.error("No connector found for this page")
-                return {
-                    "status": "error",
-                    "message": "No connector found for this page.",
-                }
-
-            notion_connector = NotionHistoryConnector(
-                session=db_session,
-                connector_id=actual_connector_id,
-            )
-
-            result = await notion_connector.update_page(
-                page_id=final_page_id,
-                content=final_content,
-            )
-            logger.info(
-                f"update_page result: {result.get('status')} - {result.get('message', '')}"
-            )
-
-            if result.get("status") == "success" and document_id is not None:
-                from app.services.notion import NotionKBSyncService
-
-                logger.info(f"Updating knowledge base for document {document_id}...")
-                kb_service = NotionKBSyncService(db_session)
-                kb_result = await kb_service.sync_after_update(
-                    document_id=document_id,
-                    appended_content=final_content,
-                    user_id=user_id,
-                    search_space_id=search_space_id,
-                    appended_block_ids=result.get("appended_block_ids"),
+            async with async_session_maker() as db_session:
+                metadata_service = NotionToolMetadataService(db_session)
+                context = await metadata_service.get_update_context(
+                    search_space_id, user_id, page_title
                 )
 
-                if kb_result["status"] == "success":
-                    result["message"] = (
-                        f"{result['message']}. Your knowledge base has also been updated."
-                    )
-                    logger.info(
-                        f"Knowledge base successfully updated for page {final_page_id}"
-                    )
-                elif kb_result["status"] == "not_indexed":
-                    result["message"] = (
-                        f"{result['message']}. This page will be added to your knowledge base in the next scheduled sync."
-                    )
-                else:
-                    result["message"] = (
-                        f"{result['message']}. Your knowledge base will be updated in the next scheduled sync."
-                    )
+                if "error" in context:
+                    error_msg = context["error"]
+                    # Check if it's a "not found" error (softer handling for LLM)
+                    if "not found" in error_msg.lower():
+                        logger.warning(f"Page not found: {error_msg}")
+                        return {
+                            "status": "not_found",
+                            "message": error_msg,
+                        }
+                    else:
+                        logger.error(f"Failed to fetch update context: {error_msg}")
+                        return {
+                            "status": "error",
+                            "message": error_msg,
+                        }
+
+                account = context.get("account", {})
+                if account.get("auth_expired"):
                     logger.warning(
-                        f"KB update failed for page {final_page_id}: {kb_result['message']}"
+                        "Notion account %s has expired authentication",
+                        account.get("id"),
+                    )
+                    return {
+                        "status": "auth_error",
+                        "message": "The Notion account for this page needs re-authentication. Please re-authenticate in your connector settings.",
+                    }
+
+                page_id = context.get("page_id")
+                document_id = context.get("document_id")
+                connector_id_from_context = context.get("account", {}).get("id")
+
+                logger.info(
+                    f"Requesting approval for updating Notion page: '{page_title}' (page_id={page_id})"
+                )
+                result = request_approval(
+                    action_type="notion_page_update",
+                    tool_name="update_notion_page",
+                    params={
+                        "page_id": page_id,
+                        "content": content,
+                        "connector_id": connector_id_from_context,
+                    },
+                    context=context,
+                )
+
+                if result.rejected:
+                    logger.info("Notion page update rejected by user")
+                    return {
+                        "status": "rejected",
+                        "message": "User declined. Do not retry or suggest alternatives.",
+                    }
+
+                final_page_id = result.params.get("page_id", page_id)
+                final_content = result.params.get("content", content)
+                final_connector_id = result.params.get(
+                    "connector_id", connector_id_from_context
+                )
+
+                logger.info(
+                    f"Updating Notion page with final params: page_id={final_page_id}, has_content={final_content is not None}"
+                )
+
+                from sqlalchemy.future import select
+
+                from app.db import SearchSourceConnector, SearchSourceConnectorType
+
+                if final_connector_id:
+                    result = await db_session.execute(
+                        select(SearchSourceConnector).filter(
+                            SearchSourceConnector.id == final_connector_id,
+                            SearchSourceConnector.search_space_id == search_space_id,
+                            SearchSourceConnector.user_id == user_id,
+                            SearchSourceConnector.connector_type
+                            == SearchSourceConnectorType.NOTION_CONNECTOR,
+                        )
+                    )
+                    connector = result.scalars().first()
+
+                    if not connector:
+                        logger.error(
+                            f"Invalid connector_id={final_connector_id} for search_space_id={search_space_id}"
+                        )
+                        return {
+                            "status": "error",
+                            "message": "Selected Notion account is invalid or has been disconnected. Please select a valid account.",
+                        }
+                    actual_connector_id = connector.id
+                    logger.info(f"Validated Notion connector: id={actual_connector_id}")
+                else:
+                    logger.error("No connector found for this page")
+                    return {
+                        "status": "error",
+                        "message": "No connector found for this page.",
+                    }
+
+                notion_connector = NotionHistoryConnector(
+                    session=db_session,
+                    connector_id=actual_connector_id,
+                )
+
+                result = await notion_connector.update_page(
+                    page_id=final_page_id,
+                    content=final_content,
+                )
+                logger.info(
+                    f"update_page result: {result.get('status')} - {result.get('message', '')}"
+                )
+
+                if result.get("status") == "success" and document_id is not None:
+                    from app.services.notion import NotionKBSyncService
+
+                    logger.info(
+                        f"Updating knowledge base for document {document_id}..."
+                    )
+                    kb_service = NotionKBSyncService(db_session)
+                    kb_result = await kb_service.sync_after_update(
+                        document_id=document_id,
+                        appended_content=final_content,
+                        user_id=user_id,
+                        search_space_id=search_space_id,
+                        appended_block_ids=result.get("appended_block_ids"),
                     )
 
-            return result
+                    if kb_result["status"] == "success":
+                        result["message"] = (
+                            f"{result['message']}. Your knowledge base has also been updated."
+                        )
+                        logger.info(
+                            f"Knowledge base successfully updated for page {final_page_id}"
+                        )
+                    elif kb_result["status"] == "not_indexed":
+                        result["message"] = (
+                            f"{result['message']}. This page will be added to your knowledge base in the next scheduled sync."
+                        )
+                    else:
+                        result["message"] = (
+                            f"{result['message']}. Your knowledge base will be updated in the next scheduled sync."
+                        )
+                        logger.warning(
+                            f"KB update failed for page {final_page_id}: {kb_result['message']}"
+                        )
+
+                return result
 
         except Exception as e:
             from langgraph.errors import GraphInterrupt

surfsense_backend/app/agents/new_chat/tools/onedrive/create_file.py

@@ -10,7 +10,7 @@ from sqlalchemy.future import select
 
 from app.agents.new_chat.tools.hitl import request_approval
 from app.connectors.onedrive.client import OneDriveClient
-from app.db import SearchSourceConnector, SearchSourceConnectorType
+from app.db import SearchSourceConnector, SearchSourceConnectorType, async_session_maker
 
 logger = logging.getLogger(__name__)
 
@@ -48,6 +48,23 @@ def create_create_onedrive_file_tool(
     search_space_id: int | None = None,
     user_id: str | None = None,
 ):
+    """
+    Factory function to create the create_onedrive_file tool.
+
+    The tool acquires its own short-lived ``AsyncSession`` per call via
+    :data:`async_session_maker` so the closure is safe to share across
+    HTTP requests by the compiled-agent cache. Capturing a per-request
+    session here would surface stale/closed sessions on cache hits.
+
+    Args:
+        db_session: Reserved for registry compatibility. Per-call sessions
+            are opened via :data:`async_session_maker` inside the tool body.
+
+    Returns:
+        Configured create_onedrive_file tool
+    """
+    del db_session  # per-call session — see docstring
+
     @tool
     async def create_onedrive_file(
         name: str,
@@ -70,173 +87,178 @@ def create_create_onedrive_file_tool(
         """
         logger.info(f"create_onedrive_file called: name='{name}'")
 
-        if db_session is None or search_space_id is None or user_id is None:
+        if search_space_id is None or user_id is None:
             return {
                 "status": "error",
                 "message": "OneDrive tool not properly configured.",
             }
 
         try:
-            result = await db_session.execute(
-                select(SearchSourceConnector).filter(
-                    SearchSourceConnector.search_space_id == search_space_id,
-                    SearchSourceConnector.user_id == user_id,
-                    SearchSourceConnector.connector_type
-                    == SearchSourceConnectorType.ONEDRIVE_CONNECTOR,
-                )
-            )
-            connectors = result.scalars().all()
-
-            if not connectors:
-                return {
-                    "status": "error",
-                    "message": "No OneDrive connector found. Please connect OneDrive in your workspace settings.",
-                }
-
-            accounts = []
-            for c in connectors:
-                cfg = c.config or {}
-                accounts.append(
-                    {
-                        "id": c.id,
-                        "name": c.name,
-                        "user_email": cfg.get("user_email"),
-                        "auth_expired": cfg.get("auth_expired", False),
-                    }
-                )
-
-            if all(a.get("auth_expired") for a in accounts):
-                return {
-                    "status": "auth_error",
-                    "message": "All connected OneDrive accounts need re-authentication.",
-                    "connector_type": "onedrive",
-                }
-
-            parent_folders: dict[int, list[dict[str, str]]] = {}
-            for acc in accounts:
-                cid = acc["id"]
-                if acc.get("auth_expired"):
-                    parent_folders[cid] = []
-                    continue
-                try:
-                    client = OneDriveClient(session=db_session, connector_id=cid)
-                    items, err = await client.list_children("root")
-                    if err:
-                        logger.warning(
-                            "Failed to list folders for connector %s: %s", cid, err
-                        )
-                        parent_folders[cid] = []
-                    else:
-                        parent_folders[cid] = [
-                            {"folder_id": item["id"], "name": item["name"]}
-                            for item in items
-                            if item.get("folder") is not None
-                            and item.get("id")
-                            and item.get("name")
-                        ]
-                except Exception:
-                    logger.warning(
-                        "Error fetching folders for connector %s", cid, exc_info=True
-                    )
-                    parent_folders[cid] = []
-
-            context: dict[str, Any] = {
-                "accounts": accounts,
-                "parent_folders": parent_folders,
-            }
-
-            result = request_approval(
-                action_type="onedrive_file_creation",
-                tool_name="create_onedrive_file",
-                params={
-                    "name": name,
-                    "content": content,
-                    "connector_id": None,
-                    "parent_folder_id": None,
-                },
-                context=context,
-            )
-
-            if result.rejected:
-                return {
-                    "status": "rejected",
-                    "message": "User declined. Do not retry or suggest alternatives.",
-                }
-
-            final_name = result.params.get("name", name)
-            final_content = result.params.get("content", content)
-            final_connector_id = result.params.get("connector_id")
-            final_parent_folder_id = result.params.get("parent_folder_id")
-
-            if not final_name or not final_name.strip():
-                return {"status": "error", "message": "File name cannot be empty."}
-
-            final_name = _ensure_docx_extension(final_name)
-
-            if final_connector_id is not None:
+            async with async_session_maker() as db_session:
                 result = await db_session.execute(
                     select(SearchSourceConnector).filter(
-                        SearchSourceConnector.id == final_connector_id,
                         SearchSourceConnector.search_space_id == search_space_id,
                         SearchSourceConnector.user_id == user_id,
                         SearchSourceConnector.connector_type
                         == SearchSourceConnectorType.ONEDRIVE_CONNECTOR,
                     )
                 )
-                connector = result.scalars().first()
-            else:
-                connector = connectors[0]
+                connectors = result.scalars().all()
 
-            if not connector:
-                return {
-                    "status": "error",
-                    "message": "Selected OneDrive connector is invalid.",
+                if not connectors:
+                    return {
+                        "status": "error",
+                        "message": "No OneDrive connector found. Please connect OneDrive in your workspace settings.",
+                    }
+
+                accounts = []
+                for c in connectors:
+                    cfg = c.config or {}
+                    accounts.append(
+                        {
+                            "id": c.id,
+                            "name": c.name,
+                            "user_email": cfg.get("user_email"),
+                            "auth_expired": cfg.get("auth_expired", False),
+                        }
+                    )
+
+                if all(a.get("auth_expired") for a in accounts):
+                    return {
+                        "status": "auth_error",
+                        "message": "All connected OneDrive accounts need re-authentication.",
+                        "connector_type": "onedrive",
+                    }
+
+                parent_folders: dict[int, list[dict[str, str]]] = {}
+                for acc in accounts:
+                    cid = acc["id"]
+                    if acc.get("auth_expired"):
+                        parent_folders[cid] = []
+                        continue
+                    try:
+                        client = OneDriveClient(session=db_session, connector_id=cid)
+                        items, err = await client.list_children("root")
+                        if err:
+                            logger.warning(
+                                "Failed to list folders for connector %s: %s", cid, err
+                            )
+                            parent_folders[cid] = []
+                        else:
+                            parent_folders[cid] = [
+                                {"folder_id": item["id"], "name": item["name"]}
+                                for item in items
+                                if item.get("folder") is not None
+                                and item.get("id")
+                                and item.get("name")
+                            ]
+                    except Exception:
+                        logger.warning(
+                            "Error fetching folders for connector %s",
+                            cid,
+                            exc_info=True,
+                        )
+                        parent_folders[cid] = []
+
+                context: dict[str, Any] = {
+                    "accounts": accounts,
+                    "parent_folders": parent_folders,
                 }
 
-            docx_bytes = _markdown_to_docx(final_content or "")
-
-            client = OneDriveClient(session=db_session, connector_id=connector.id)
-            created = await client.create_file(
-                name=final_name,
-                parent_id=final_parent_folder_id,
-                content=docx_bytes,
-                mime_type=DOCX_MIME,
-            )
-
-            logger.info(
-                f"OneDrive file created: id={created.get('id')}, name={created.get('name')}"
-            )
-
-            kb_message_suffix = ""
-            try:
-                from app.services.onedrive import OneDriveKBSyncService
-
-                kb_service = OneDriveKBSyncService(db_session)
-                kb_result = await kb_service.sync_after_create(
-                    file_id=created.get("id"),
-                    file_name=created.get("name", final_name),
-                    mime_type=DOCX_MIME,
-                    web_url=created.get("webUrl"),
-                    content=final_content,
-                    connector_id=connector.id,
-                    search_space_id=search_space_id,
-                    user_id=user_id,
+                result = request_approval(
+                    action_type="onedrive_file_creation",
+                    tool_name="create_onedrive_file",
+                    params={
+                        "name": name,
+                        "content": content,
+                        "connector_id": None,
+                        "parent_folder_id": None,
+                    },
+                    context=context,
                 )
-                if kb_result["status"] == "success":
-                    kb_message_suffix = " Your knowledge base has also been updated."
-                else:
-                    kb_message_suffix = " This file will be added to your knowledge base in the next scheduled sync."
-            except Exception as kb_err:
-                logger.warning(f"KB sync after create failed: {kb_err}")
-                kb_message_suffix = " This file will be added to your knowledge base in the next scheduled sync."
 
-            return {
-                "status": "success",
-                "file_id": created.get("id"),
-                "name": created.get("name"),
-                "web_url": created.get("webUrl"),
-                "message": f"Successfully created '{created.get('name')}' in OneDrive.{kb_message_suffix}",
-            }
+                if result.rejected:
+                    return {
+                        "status": "rejected",
+                        "message": "User declined. Do not retry or suggest alternatives.",
+                    }
+
+                final_name = result.params.get("name", name)
+                final_content = result.params.get("content", content)
+                final_connector_id = result.params.get("connector_id")
+                final_parent_folder_id = result.params.get("parent_folder_id")
+
+                if not final_name or not final_name.strip():
+                    return {"status": "error", "message": "File name cannot be empty."}
+
+                final_name = _ensure_docx_extension(final_name)
+
+                if final_connector_id is not None:
+                    result = await db_session.execute(
+                        select(SearchSourceConnector).filter(
+                            SearchSourceConnector.id == final_connector_id,
+                            SearchSourceConnector.search_space_id == search_space_id,
+                            SearchSourceConnector.user_id == user_id,
+                            SearchSourceConnector.connector_type
+                            == SearchSourceConnectorType.ONEDRIVE_CONNECTOR,
+                        )
+                    )
+                    connector = result.scalars().first()
+                else:
+                    connector = connectors[0]
+
+                if not connector:
+                    return {
+                        "status": "error",
+                        "message": "Selected OneDrive connector is invalid.",
+                    }
+
+                docx_bytes = _markdown_to_docx(final_content or "")
+
+                client = OneDriveClient(session=db_session, connector_id=connector.id)
+                created = await client.create_file(
+                    name=final_name,
+                    parent_id=final_parent_folder_id,
+                    content=docx_bytes,
+                    mime_type=DOCX_MIME,
+                )
+
+                logger.info(
+                    f"OneDrive file created: id={created.get('id')}, name={created.get('name')}"
+                )
+
+                kb_message_suffix = ""
+                try:
+                    from app.services.onedrive import OneDriveKBSyncService
+
+                    kb_service = OneDriveKBSyncService(db_session)
+                    kb_result = await kb_service.sync_after_create(
+                        file_id=created.get("id"),
+                        file_name=created.get("name", final_name),
+                        mime_type=DOCX_MIME,
+                        web_url=created.get("webUrl"),
+                        content=final_content,
+                        connector_id=connector.id,
+                        search_space_id=search_space_id,
+                        user_id=user_id,
+                    )
+                    if kb_result["status"] == "success":
+                        kb_message_suffix = (
+                            " Your knowledge base has also been updated."
+                        )
+                    else:
+                        kb_message_suffix = " This file will be added to your knowledge base in the next scheduled sync."
+                except Exception as kb_err:
+                    logger.warning(f"KB sync after create failed: {kb_err}")
+                    kb_message_suffix = " This file will be added to your knowledge base in the next scheduled sync."
+
+                return {
+                    "status": "success",
+                    "file_id": created.get("id"),
+                    "name": created.get("name"),
+                    "web_url": created.get("webUrl"),
+                    "message": f"Successfully created '{created.get('name')}' in OneDrive.{kb_message_suffix}",
+                }
 
         except Exception as e:
             from langgraph.errors import GraphInterrupt

surfsense_backend/app/agents/new_chat/tools/onedrive/trash_file.py

@@ -13,6 +13,7 @@ from app.db import (
     DocumentType,
     SearchSourceConnector,
     SearchSourceConnectorType,
+    async_session_maker,
 )
 
 logger = logging.getLogger(__name__)
@@ -23,6 +24,23 @@ def create_delete_onedrive_file_tool(
     search_space_id: int | None = None,
     user_id: str | None = None,
 ):
+    """
+    Factory function to create the delete_onedrive_file tool.
+
+    The tool acquires its own short-lived ``AsyncSession`` per call via
+    :data:`async_session_maker` so the closure is safe to share across
+    HTTP requests by the compiled-agent cache. Capturing a per-request
+    session here would surface stale/closed sessions on cache hits.
+
+    Args:
+        db_session: Reserved for registry compatibility. Per-call sessions
+            are opened via :data:`async_session_maker` inside the tool body.
+
+    Returns:
+        Configured delete_onedrive_file tool
+    """
+    del db_session  # per-call session — see docstring
+
     @tool
     async def delete_onedrive_file(
         file_name: str,
@@ -56,33 +74,14 @@ def create_delete_onedrive_file_tool(
             f"delete_onedrive_file called: file_name='{file_name}', delete_from_kb={delete_from_kb}"
         )
 
-        if db_session is None or search_space_id is None or user_id is None:
+        if search_space_id is None or user_id is None:
             return {
                 "status": "error",
                 "message": "OneDrive tool not properly configured.",
             }
 
         try:
-            doc_result = await db_session.execute(
-                select(Document)
-                .join(
-                    SearchSourceConnector,
-                    Document.connector_id == SearchSourceConnector.id,
-                )
-                .filter(
-                    and_(
-                        Document.search_space_id == search_space_id,
-                        Document.document_type == DocumentType.ONEDRIVE_FILE,
-                        func.lower(Document.title) == func.lower(file_name),
-                        SearchSourceConnector.user_id == user_id,
-                    )
-                )
-                .order_by(Document.updated_at.desc().nullslast())
-                .limit(1)
-            )
-            document = doc_result.scalars().first()
-
-            if not document:
+            async with async_session_maker() as db_session:
                 doc_result = await db_session.execute(
                     select(Document)
                     .join(
@@ -93,13 +92,7 @@ def create_delete_onedrive_file_tool(
                         and_(
                             Document.search_space_id == search_space_id,
                             Document.document_type == DocumentType.ONEDRIVE_FILE,
-                            func.lower(
-                                cast(
-                                    Document.document_metadata["onedrive_file_name"],
-                                    String,
-                                )
-                            )
-                            == func.lower(file_name),
+                            func.lower(Document.title) == func.lower(file_name),
                             SearchSourceConnector.user_id == user_id,
                         )
                     )
@@ -108,98 +101,64 @@ def create_delete_onedrive_file_tool(
                 )
                 document = doc_result.scalars().first()
 
-            if not document:
-                return {
-                    "status": "not_found",
-                    "message": (
-                        f"File '{file_name}' not found in your indexed OneDrive files. "
-                        "This could mean: (1) the file doesn't exist, (2) it hasn't been indexed yet, "
-                        "or (3) the file name is different."
-                    ),
-                }
-
-            if not document.connector_id:
-                return {
-                    "status": "error",
-                    "message": "Document has no associated connector.",
-                }
-
-            meta = document.document_metadata or {}
-            file_id = meta.get("onedrive_file_id")
-            document_id = document.id
-
-            if not file_id:
-                return {
-                    "status": "error",
-                    "message": "File ID is missing. Please re-index the file.",
-                }
-
-            conn_result = await db_session.execute(
-                select(SearchSourceConnector).filter(
-                    and_(
-                        SearchSourceConnector.id == document.connector_id,
-                        SearchSourceConnector.search_space_id == search_space_id,
-                        SearchSourceConnector.user_id == user_id,
-                        SearchSourceConnector.connector_type
-                        == SearchSourceConnectorType.ONEDRIVE_CONNECTOR,
+                if not document:
+                    doc_result = await db_session.execute(
+                        select(Document)
+                        .join(
+                            SearchSourceConnector,
+                            Document.connector_id == SearchSourceConnector.id,
+                        )
+                        .filter(
+                            and_(
+                                Document.search_space_id == search_space_id,
+                                Document.document_type == DocumentType.ONEDRIVE_FILE,
+                                func.lower(
+                                    cast(
+                                        Document.document_metadata[
+                                            "onedrive_file_name"
+                                        ],
+                                        String,
+                                    )
+                                )
+                                == func.lower(file_name),
+                                SearchSourceConnector.user_id == user_id,
+                            )
+                        )
+                        .order_by(Document.updated_at.desc().nullslast())
+                        .limit(1)
                     )
-                )
-            )
-            connector = conn_result.scalars().first()
-            if not connector:
-                return {
-                    "status": "error",
-                    "message": "OneDrive connector not found or access denied.",
-                }
+                    document = doc_result.scalars().first()
 
-            cfg = connector.config or {}
-            if cfg.get("auth_expired"):
-                return {
-                    "status": "auth_error",
-                    "message": "OneDrive account needs re-authentication. Please re-authenticate in your connector settings.",
-                    "connector_type": "onedrive",
-                }
+                if not document:
+                    return {
+                        "status": "not_found",
+                        "message": (
+                            f"File '{file_name}' not found in your indexed OneDrive files. "
+                            "This could mean: (1) the file doesn't exist, (2) it hasn't been indexed yet, "
+                            "or (3) the file name is different."
+                        ),
+                    }
 
-            context = {
-                "file": {
-                    "file_id": file_id,
-                    "name": file_name,
-                    "document_id": document_id,
-                    "web_url": meta.get("web_url"),
-                },
-                "account": {
-                    "id": connector.id,
-                    "name": connector.name,
-                    "user_email": cfg.get("user_email"),
-                },
-            }
+                if not document.connector_id:
+                    return {
+                        "status": "error",
+                        "message": "Document has no associated connector.",
+                    }
 
-            result = request_approval(
-                action_type="onedrive_file_trash",
-                tool_name="delete_onedrive_file",
-                params={
-                    "file_id": file_id,
-                    "connector_id": connector.id,
-                    "delete_from_kb": delete_from_kb,
-                },
-                context=context,
-            )
+                meta = document.document_metadata or {}
+                file_id = meta.get("onedrive_file_id")
+                document_id = document.id
 
-            if result.rejected:
-                return {
-                    "status": "rejected",
-                    "message": "User declined. Do not retry or suggest alternatives.",
-                }
+                if not file_id:
+                    return {
+                        "status": "error",
+                        "message": "File ID is missing. Please re-index the file.",
+                    }
 
-            final_file_id = result.params.get("file_id", file_id)
-            final_connector_id = result.params.get("connector_id", connector.id)
-            final_delete_from_kb = result.params.get("delete_from_kb", delete_from_kb)
-
-            if final_connector_id != connector.id:
-                result = await db_session.execute(
+                conn_result = await db_session.execute(
                     select(SearchSourceConnector).filter(
                         and_(
-                            SearchSourceConnector.id == final_connector_id,
+                            SearchSourceConnector.id == document.connector_id,
                             SearchSourceConnector.search_space_id == search_space_id,
                             SearchSourceConnector.user_id == user_id,
                             SearchSourceConnector.connector_type
@@ -207,65 +166,130 @@ def create_delete_onedrive_file_tool(
                         )
                     )
                 )
-                validated_connector = result.scalars().first()
-                if not validated_connector:
+                connector = conn_result.scalars().first()
+                if not connector:
                     return {
                         "status": "error",
-                        "message": "Selected OneDrive connector is invalid or has been disconnected.",
+                        "message": "OneDrive connector not found or access denied.",
                     }
-                actual_connector_id = validated_connector.id
-            else:
-                actual_connector_id = connector.id
 
-            logger.info(
-                f"Deleting OneDrive file: file_id='{final_file_id}', connector={actual_connector_id}"
-            )
+                cfg = connector.config or {}
+                if cfg.get("auth_expired"):
+                    return {
+                        "status": "auth_error",
+                        "message": "OneDrive account needs re-authentication. Please re-authenticate in your connector settings.",
+                        "connector_type": "onedrive",
+                    }
 
-            client = OneDriveClient(
-                session=db_session, connector_id=actual_connector_id
-            )
-            await client.trash_file(final_file_id)
+                context = {
+                    "file": {
+                        "file_id": file_id,
+                        "name": file_name,
+                        "document_id": document_id,
+                        "web_url": meta.get("web_url"),
+                    },
+                    "account": {
+                        "id": connector.id,
+                        "name": connector.name,
+                        "user_email": cfg.get("user_email"),
+                    },
+                }
 
-            logger.info(
-                f"OneDrive file deleted (moved to recycle bin): file_id={final_file_id}"
-            )
-
-            trash_result: dict[str, Any] = {
-                "status": "success",
-                "file_id": final_file_id,
-                "message": f"Successfully moved '{file_name}' to the recycle bin.",
-            }
-
-            deleted_from_kb = False
-            if final_delete_from_kb and document_id:
-                try:
-                    doc_result = await db_session.execute(
-                        select(Document).filter(Document.id == document_id)
-                    )
-                    doc = doc_result.scalars().first()
-                    if doc:
-                        await db_session.delete(doc)
-                        await db_session.commit()
-                        deleted_from_kb = True
-                        logger.info(
-                            f"Deleted document {document_id} from knowledge base"
-                        )
-                    else:
-                        logger.warning(f"Document {document_id} not found in KB")
-                except Exception as e:
-                    logger.error(f"Failed to delete document from KB: {e}")
-                    await db_session.rollback()
-                    trash_result["warning"] = (
-                        f"File moved to recycle bin, but failed to remove from knowledge base: {e!s}"
-                    )
-
-            trash_result["deleted_from_kb"] = deleted_from_kb
-            if deleted_from_kb:
-                trash_result["message"] = (
-                    f"{trash_result.get('message', '')} (also removed from knowledge base)"
+                result = request_approval(
+                    action_type="onedrive_file_trash",
+                    tool_name="delete_onedrive_file",
+                    params={
+                        "file_id": file_id,
+                        "connector_id": connector.id,
+                        "delete_from_kb": delete_from_kb,
+                    },
+                    context=context,
                 )
 
-            return trash_result
+                if result.rejected:
+                    return {
+                        "status": "rejected",
+                        "message": "User declined. Do not retry or suggest alternatives.",
+                    }
+
+                final_file_id = result.params.get("file_id", file_id)
+                final_connector_id = result.params.get("connector_id", connector.id)
+                final_delete_from_kb = result.params.get(
+                    "delete_from_kb", delete_from_kb
+                )
+
+                if final_connector_id != connector.id:
+                    result = await db_session.execute(
+                        select(SearchSourceConnector).filter(
+                            and_(
+                                SearchSourceConnector.id == final_connector_id,
+                                SearchSourceConnector.search_space_id
+                                == search_space_id,
+                                SearchSourceConnector.user_id == user_id,
+                                SearchSourceConnector.connector_type
+                                == SearchSourceConnectorType.ONEDRIVE_CONNECTOR,
+                            )
+                        )
+                    )
+                    validated_connector = result.scalars().first()
+                    if not validated_connector:
+                        return {
+                            "status": "error",
+                            "message": "Selected OneDrive connector is invalid or has been disconnected.",
+                        }
+                    actual_connector_id = validated_connector.id
+                else:
+                    actual_connector_id = connector.id
+
+                logger.info(
+                    f"Deleting OneDrive file: file_id='{final_file_id}', connector={actual_connector_id}"
+                )
+
+                client = OneDriveClient(
+                    session=db_session, connector_id=actual_connector_id
+                )
+                await client.trash_file(final_file_id)
+
+                logger.info(
+                    f"OneDrive file deleted (moved to recycle bin): file_id={final_file_id}"
+                )
+
+                trash_result: dict[str, Any] = {
+                    "status": "success",
+                    "file_id": final_file_id,
+                    "message": f"Successfully moved '{file_name}' to the recycle bin.",
+                }
+
+                deleted_from_kb = False
+                if final_delete_from_kb and document_id:
+                    try:
+                        doc_result = await db_session.execute(
+                            select(Document).filter(Document.id == document_id)
+                        )
+                        doc = doc_result.scalars().first()
+                        if doc:
+                            await db_session.delete(doc)
+                            await db_session.commit()
+                            deleted_from_kb = True
+                            logger.info(
+                                f"Deleted document {document_id} from knowledge base"
+                            )
+                        else:
+                            logger.warning(f"Document {document_id} not found in KB")
+                    except Exception as e:
+                        logger.error(f"Failed to delete document from KB: {e}")
+                        await db_session.rollback()
+                        trash_result["warning"] = (
+                            f"File moved to recycle bin, but failed to remove from knowledge base: {e!s}"
+                        )
+
+                trash_result["deleted_from_kb"] = deleted_from_kb
+                if deleted_from_kb:
+                    trash_result["message"] = (
+                        f"{trash_result.get('message', '')} (also removed from knowledge base)"
+                    )
+
+                return trash_result
 
         except Exception as e:
             from langgraph.errors import GraphInterrupt

surfsense_backend/app/agents/new_chat/tools/registry.py

@@ -824,13 +824,22 @@ async def build_tools_async(
     """Async version of build_tools that also loads MCP tools from database.
 
     Design Note:
-    This function exists because MCP tools require database queries to load user configs,
-    while built-in tools are created synchronously from static code.
+    This function exists because MCP tools require database queries to load
+    user configs, while built-in tools are created synchronously from static
+    code.
 
-    Alternative: We could make build_tools() itself async and always query the database,
-    but that would force async everywhere even when only using built-in tools. The current
-    design keeps the simple case (static tools only) synchronous while supporting dynamic
-    database-loaded tools through this async wrapper.
+    Alternative: We could make build_tools() itself async and always query
+    the database, but that would force async everywhere even when only using
+    built-in tools. The current design keeps the simple case (static tools
+    only) synchronous while supporting dynamic database-loaded tools through
+    this async wrapper.
+
+    Phase 1.3: built-in tool construction (CPU; runs in a thread pool to
+    avoid event-loop stalls) and MCP tool loading (HTTP/DB I/O; runs on
+    the event loop) are kicked off concurrently. Cold-path savings are
+    bounded by the slower of the two — typically MCP at ~200ms-1.7s —
+    so the parallelization recovers the ~50-200ms previously spent
+    serially on built-in construction.
 
     Args:
         dependencies: Dict containing all possible dependencies
@@ -843,33 +852,70 @@ async def build_tools_async(
         List of configured tool instances ready for the agent, including MCP tools.
 
     """
+    import asyncio
     import time
 
     _perf_log = logging.getLogger("surfsense.perf")
     _perf_log.setLevel(logging.DEBUG)
 
+    can_load_mcp = (
+        include_mcp_tools
+        and "db_session" in dependencies
+        and "search_space_id" in dependencies
+    )
+
+    # Built-in tool construction is synchronous + CPU-only. Off-loop it so
+    # MCP's HTTP/DB I/O can fire concurrently. ``build_tools`` is pure
+    # function over its inputs — safe to thread-shift.
     _t0 = time.perf_counter()
-    tools = build_tools(dependencies, enabled_tools, disabled_tools, additional_tools)
+    builtin_task = asyncio.create_task(
+        asyncio.to_thread(
+            build_tools, dependencies, enabled_tools, disabled_tools, additional_tools
+        )
+    )
+
+    mcp_task: asyncio.Task | None = None
+    if can_load_mcp:
+        mcp_task = asyncio.create_task(
+            load_mcp_tools(
+                dependencies["db_session"],
+                dependencies["search_space_id"],
+            )
+        )
+
+    # Surface failures from each task independently so a flaky MCP
+    # endpoint never poisons built-in tool registration. ``return_exceptions``
+    # gives us per-task exceptions instead of dropping the second result
+    # when the first raises.
+    if mcp_task is not None:
+        builtin_result, mcp_result = await asyncio.gather(
+            builtin_task, mcp_task, return_exceptions=True
+        )
+    else:
+        builtin_result = await builtin_task
+        mcp_result = None
+
+    if isinstance(builtin_result, BaseException):
+        raise builtin_result  # built-in registration failure is non-recoverable
+    tools: list[BaseTool] = builtin_result
     _perf_log.info(
-        "[build_tools_async] Built-in tools in %.3fs (%d tools)",
+        "[build_tools_async] Built-in tools in %.3fs (%d tools, parallel)",
         time.perf_counter() - _t0,
         len(tools),
     )
 
-    # Load MCP tools if requested and dependencies are available
-    if (
-        include_mcp_tools
-        and "db_session" in dependencies
-        and "search_space_id" in dependencies
-    ):
-        try:
-            _t0 = time.perf_counter()
-            mcp_tools = await load_mcp_tools(
-                dependencies["db_session"],
-                dependencies["search_space_id"],
+    if mcp_task is not None:
+        if isinstance(mcp_result, BaseException):
+            # ``return_exceptions=True`` captures the exception out-of-band,
+            # so ``sys.exc_info()`` is empty here. Pass the captured
+            # exception via ``exc_info=`` to get a real traceback.
+            logging.error(
+                "Failed to load MCP tools: %s", mcp_result, exc_info=mcp_result
             )
+        else:
+            mcp_tools = mcp_result or []
             _perf_log.info(
-                "[build_tools_async] MCP tools loaded in %.3fs (%d tools)",
+                "[build_tools_async] MCP tools loaded in %.3fs (%d tools, parallel)",
                 time.perf_counter() - _t0,
                 len(mcp_tools),
             )
@@ -879,8 +925,6 @@ async def build_tools_async(
                 len(mcp_tools),
                 [t.name for t in mcp_tools],
             )
-        except Exception as e:
-            logging.exception("Failed to load MCP tools: %s", e)
 
     logging.info(
         "Total tools for agent: %d — %s",

surfsense_backend/app/agents/new_chat/tools/search_surfsense_docs.py

@@ -15,7 +15,7 @@ from langchain_core.tools import tool
 from sqlalchemy import select
 from sqlalchemy.ext.asyncio import AsyncSession
 
-from app.db import SurfsenseDocsChunk, SurfsenseDocsDocument
+from app.db import SurfsenseDocsChunk, SurfsenseDocsDocument, async_session_maker
 from app.utils.document_converters import embed_text
 
 
@@ -124,12 +124,19 @@ def create_search_surfsense_docs_tool(db_session: AsyncSession):
     """
     Factory function to create the search_surfsense_docs tool.
 
+    The tool acquires its own short-lived ``AsyncSession`` per call via
+    :data:`async_session_maker` so the closure is safe to share across
+    HTTP requests by the compiled-agent cache. Capturing a per-request
+    session here would surface stale/closed sessions on cache hits.
+
     Args:
-        db_session: Database session for executing queries
+        db_session: Reserved for registry compatibility. Per-call sessions
+            are opened via :data:`async_session_maker` inside the tool body.
 
     Returns:
         A configured tool function for searching Surfsense documentation
     """
+    del db_session  # per-call session — see docstring
 
     @tool
     async def search_surfsense_docs(query: str, top_k: int = 10) -> str:
@@ -155,10 +162,11 @@ def create_search_surfsense_docs_tool(db_session: AsyncSession):
         Returns:
             Relevant documentation content formatted with chunk IDs for citations
         """
-        return await search_surfsense_docs_async(
-            query=query,
-            db_session=db_session,
-            top_k=top_k,
-        )
+        async with async_session_maker() as db_session:
+            return await search_surfsense_docs_async(
+                query=query,
+                db_session=db_session,
+                top_k=top_k,
+            )
 
     return search_surfsense_docs

surfsense_backend/app/agents/new_chat/tools/teams/list_channels.py

@@ -5,6 +5,8 @@ import httpx
 from langchain_core.tools import tool
 from sqlalchemy.ext.asyncio import AsyncSession
 
+from app.db import async_session_maker
+
 from ._auth import GRAPH_API, get_access_token, get_teams_connector
 
 logger = logging.getLogger(__name__)
@@ -15,6 +17,23 @@ def create_list_teams_channels_tool(
     search_space_id: int | None = None,
     user_id: str | None = None,
 ):
+    """
+    Factory function to create the list_teams_channels tool.
+
+    The tool acquires its own short-lived ``AsyncSession`` per call via
+    :data:`async_session_maker` so the closure is safe to share across
+    HTTP requests by the compiled-agent cache. Capturing a per-request
+    session here would surface stale/closed sessions on cache hits.
+
+    Args:
+        db_session: Reserved for registry compatibility. Per-call sessions
+            are opened via :data:`async_session_maker` inside the tool body.
+
+    Returns:
+        Configured list_teams_channels tool
+    """
+    del db_session  # per-call session — see docstring
+
     @tool
     async def list_teams_channels() -> dict[str, Any]:
         """List all Microsoft Teams and their channels the user has access to.
@@ -23,63 +42,66 @@ def create_list_teams_channels_tool(
             Dictionary with status and a list of teams, each containing
             team_id, team_name, and a list of channels (id, name).
         """
-        if db_session is None or search_space_id is None or user_id is None:
+        if search_space_id is None or user_id is None:
             return {"status": "error", "message": "Teams tool not properly configured."}
 
         try:
-            connector = await get_teams_connector(db_session, search_space_id, user_id)
-            if not connector:
-                return {"status": "error", "message": "No Teams connector found."}
-
-            token = await get_access_token(db_session, connector)
-            headers = {"Authorization": f"Bearer {token}"}
-
-            async with httpx.AsyncClient(timeout=20.0) as client:
-                teams_resp = await client.get(
-                    f"{GRAPH_API}/me/joinedTeams", headers=headers
+            async with async_session_maker() as db_session:
+                connector = await get_teams_connector(
+                    db_session, search_space_id, user_id
                 )
+                if not connector:
+                    return {"status": "error", "message": "No Teams connector found."}
 
-            if teams_resp.status_code == 401:
-                return {
-                    "status": "auth_error",
-                    "message": "Teams token expired. Please re-authenticate.",
-                    "connector_type": "teams",
-                }
-            if teams_resp.status_code != 200:
-                return {
-                    "status": "error",
-                    "message": f"Graph API error: {teams_resp.status_code}",
-                }
+                token = await get_access_token(db_session, connector)
+                headers = {"Authorization": f"Bearer {token}"}
 
-            teams_data = teams_resp.json().get("value", [])
-            result_teams = []
-
-            async with httpx.AsyncClient(timeout=20.0) as client:
-                for team in teams_data:
-                    team_id = team["id"]
-                    ch_resp = await client.get(
-                        f"{GRAPH_API}/teams/{team_id}/channels",
-                        headers=headers,
-                    )
-                    channels = []
-                    if ch_resp.status_code == 200:
-                        channels = [
-                            {"id": ch["id"], "name": ch.get("displayName", "")}
-                            for ch in ch_resp.json().get("value", [])
-                        ]
-                    result_teams.append(
-                        {
-                            "team_id": team_id,
-                            "team_name": team.get("displayName", ""),
-                            "channels": channels,
-                        }
+                async with httpx.AsyncClient(timeout=20.0) as client:
+                    teams_resp = await client.get(
+                        f"{GRAPH_API}/me/joinedTeams", headers=headers
                     )
 
-            return {
-                "status": "success",
-                "teams": result_teams,
-                "total_teams": len(result_teams),
-            }
+                if teams_resp.status_code == 401:
+                    return {
+                        "status": "auth_error",
+                        "message": "Teams token expired. Please re-authenticate.",
+                        "connector_type": "teams",
+                    }
+                if teams_resp.status_code != 200:
+                    return {
+                        "status": "error",
+                        "message": f"Graph API error: {teams_resp.status_code}",
+                    }
+
+                teams_data = teams_resp.json().get("value", [])
+                result_teams = []
+
+                async with httpx.AsyncClient(timeout=20.0) as client:
+                    for team in teams_data:
+                        team_id = team["id"]
+                        ch_resp = await client.get(
+                            f"{GRAPH_API}/teams/{team_id}/channels",
+                            headers=headers,
+                        )
+                        channels = []
+                        if ch_resp.status_code == 200:
+                            channels = [
+                                {"id": ch["id"], "name": ch.get("displayName", "")}
+                                for ch in ch_resp.json().get("value", [])
+                            ]
+                        result_teams.append(
+                            {
+                                "team_id": team_id,
+                                "team_name": team.get("displayName", ""),
+                                "channels": channels,
+                            }
+                        )
+
+                return {
+                    "status": "success",
+                    "teams": result_teams,
+                    "total_teams": len(result_teams),
+                }
 
         except Exception as e:
             from langgraph.errors import GraphInterrupt

surfsense_backend/app/agents/new_chat/tools/teams/read_messages.py

@@ -5,6 +5,8 @@ import httpx
 from langchain_core.tools import tool
 from sqlalchemy.ext.asyncio import AsyncSession
 
+from app.db import async_session_maker
+
 from ._auth import GRAPH_API, get_access_token, get_teams_connector
 
 logger = logging.getLogger(__name__)
@@ -15,6 +17,23 @@ def create_read_teams_messages_tool(
     search_space_id: int | None = None,
     user_id: str | None = None,
 ):
+    """
+    Factory function to create the read_teams_messages tool.
+
+    The tool acquires its own short-lived ``AsyncSession`` per call via
+    :data:`async_session_maker` so the closure is safe to share across
+    HTTP requests by the compiled-agent cache. Capturing a per-request
+    session here would surface stale/closed sessions on cache hits.
+
+    Args:
+        db_session: Reserved for registry compatibility. Per-call sessions
+            are opened via :data:`async_session_maker` inside the tool body.
+
+    Returns:
+        Configured read_teams_messages tool
+    """
+    del db_session  # per-call session — see docstring
+
     @tool
     async def read_teams_messages(
         team_id: str,
@@ -32,65 +51,68 @@ def create_read_teams_messages_tool(
             Dictionary with status and a list of messages including
             id, sender, content, timestamp.
         """
-        if db_session is None or search_space_id is None or user_id is None:
+        if search_space_id is None or user_id is None:
             return {"status": "error", "message": "Teams tool not properly configured."}
 
         limit = min(limit, 50)
 
         try:
-            connector = await get_teams_connector(db_session, search_space_id, user_id)
-            if not connector:
-                return {"status": "error", "message": "No Teams connector found."}
-
-            token = await get_access_token(db_session, connector)
-
-            async with httpx.AsyncClient(timeout=20.0) as client:
-                resp = await client.get(
-                    f"{GRAPH_API}/teams/{team_id}/channels/{channel_id}/messages",
-                    headers={"Authorization": f"Bearer {token}"},
-                    params={"$top": limit},
+            async with async_session_maker() as db_session:
+                connector = await get_teams_connector(
+                    db_session, search_space_id, user_id
                 )
+                if not connector:
+                    return {"status": "error", "message": "No Teams connector found."}
 
-            if resp.status_code == 401:
-                return {
-                    "status": "auth_error",
-                    "message": "Teams token expired. Please re-authenticate.",
-                    "connector_type": "teams",
-                }
-            if resp.status_code == 403:
-                return {
-                    "status": "error",
-                    "message": "Insufficient permissions to read this channel.",
-                }
-            if resp.status_code != 200:
-                return {
-                    "status": "error",
-                    "message": f"Graph API error: {resp.status_code}",
-                }
+                token = await get_access_token(db_session, connector)
 
-            raw_msgs = resp.json().get("value", [])
-            messages = []
-            for m in raw_msgs:
-                sender = m.get("from", {})
-                user_info = sender.get("user", {}) if sender else {}
-                body = m.get("body", {})
-                messages.append(
-                    {
-                        "id": m.get("id"),
-                        "sender": user_info.get("displayName", "Unknown"),
-                        "content": body.get("content", ""),
-                        "content_type": body.get("contentType", "text"),
-                        "timestamp": m.get("createdDateTime", ""),
+                async with httpx.AsyncClient(timeout=20.0) as client:
+                    resp = await client.get(
+                        f"{GRAPH_API}/teams/{team_id}/channels/{channel_id}/messages",
+                        headers={"Authorization": f"Bearer {token}"},
+                        params={"$top": limit},
+                    )
+
+                if resp.status_code == 401:
+                    return {
+                        "status": "auth_error",
+                        "message": "Teams token expired. Please re-authenticate.",
+                        "connector_type": "teams",
+                    }
+                if resp.status_code == 403:
+                    return {
+                        "status": "error",
+                        "message": "Insufficient permissions to read this channel.",
+                    }
+                if resp.status_code != 200:
+                    return {
+                        "status": "error",
+                        "message": f"Graph API error: {resp.status_code}",
                     }
-                )
 
-            return {
-                "status": "success",
-                "team_id": team_id,
-                "channel_id": channel_id,
-                "messages": messages,
-                "total": len(messages),
-            }
+                raw_msgs = resp.json().get("value", [])
+                messages = []
+                for m in raw_msgs:
+                    sender = m.get("from", {})
+                    user_info = sender.get("user", {}) if sender else {}
+                    body = m.get("body", {})
+                    messages.append(
+                        {
+                            "id": m.get("id"),
+                            "sender": user_info.get("displayName", "Unknown"),
+                            "content": body.get("content", ""),
+                            "content_type": body.get("contentType", "text"),
+                            "timestamp": m.get("createdDateTime", ""),
+                        }
+                    )
+
+                return {
+                    "status": "success",
+                    "team_id": team_id,
+                    "channel_id": channel_id,
+                    "messages": messages,
+                    "total": len(messages),
+                }
 
         except Exception as e:
             from langgraph.errors import GraphInterrupt

surfsense_backend/app/agents/new_chat/tools/teams/send_message.py

@@ -6,6 +6,7 @@ from langchain_core.tools import tool
 from sqlalchemy.ext.asyncio import AsyncSession
 
 from app.agents.new_chat.tools.hitl import request_approval
+from app.db import async_session_maker
 
 from ._auth import GRAPH_API, get_access_token, get_teams_connector
 
@@ -17,6 +18,23 @@ def create_send_teams_message_tool(
     search_space_id: int | None = None,
     user_id: str | None = None,
 ):
+    """
+    Factory function to create the send_teams_message tool.
+
+    The tool acquires its own short-lived ``AsyncSession`` per call via
+    :data:`async_session_maker` so the closure is safe to share across
+    HTTP requests by the compiled-agent cache. Capturing a per-request
+    session here would surface stale/closed sessions on cache hits.
+
+    Args:
+        db_session: Reserved for registry compatibility. Per-call sessions
+            are opened via :data:`async_session_maker` inside the tool body.
+
+    Returns:
+        Configured send_teams_message tool
+    """
+    del db_session  # per-call session — see docstring
+
     @tool
     async def send_teams_message(
         team_id: str,
@@ -39,70 +57,73 @@ def create_send_teams_message_tool(
             IMPORTANT:
             - If status is "rejected", the user explicitly declined. Do NOT retry.
         """
-        if db_session is None or search_space_id is None or user_id is None:
+        if search_space_id is None or user_id is None:
             return {"status": "error", "message": "Teams tool not properly configured."}
 
         try:
-            connector = await get_teams_connector(db_session, search_space_id, user_id)
-            if not connector:
-                return {"status": "error", "message": "No Teams connector found."}
+            async with async_session_maker() as db_session:
+                connector = await get_teams_connector(
+                    db_session, search_space_id, user_id
+                )
+                if not connector:
+                    return {"status": "error", "message": "No Teams connector found."}
 
-            result = request_approval(
-                action_type="teams_send_message",
-                tool_name="send_teams_message",
-                params={
-                    "team_id": team_id,
-                    "channel_id": channel_id,
-                    "content": content,
-                },
-                context={"connector_id": connector.id},
-            )
-
-            if result.rejected:
-                return {
-                    "status": "rejected",
-                    "message": "User declined. Message was not sent.",
-                }
-
-            final_content = result.params.get("content", content)
-            final_team = result.params.get("team_id", team_id)
-            final_channel = result.params.get("channel_id", channel_id)
-
-            token = await get_access_token(db_session, connector)
-
-            async with httpx.AsyncClient(timeout=20.0) as client:
-                resp = await client.post(
-                    f"{GRAPH_API}/teams/{final_team}/channels/{final_channel}/messages",
-                    headers={
-                        "Authorization": f"Bearer {token}",
-                        "Content-Type": "application/json",
+                result = request_approval(
+                    action_type="teams_send_message",
+                    tool_name="send_teams_message",
+                    params={
+                        "team_id": team_id,
+                        "channel_id": channel_id,
+                        "content": content,
                     },
-                    json={"body": {"content": final_content}},
+                    context={"connector_id": connector.id},
                 )
 
-            if resp.status_code == 401:
-                return {
-                    "status": "auth_error",
-                    "message": "Teams token expired. Please re-authenticate.",
-                    "connector_type": "teams",
-                }
-            if resp.status_code == 403:
-                return {
-                    "status": "insufficient_permissions",
-                    "message": "Missing ChannelMessage.Send permission. Please re-authenticate with updated scopes.",
-                }
-            if resp.status_code not in (200, 201):
-                return {
-                    "status": "error",
-                    "message": f"Graph API error: {resp.status_code} — {resp.text[:200]}",
-                }
+                if result.rejected:
+                    return {
+                        "status": "rejected",
+                        "message": "User declined. Message was not sent.",
+                    }
 
-            msg_data = resp.json()
-            return {
-                "status": "success",
-                "message_id": msg_data.get("id"),
-                "message": "Message sent to Teams channel.",
-            }
+                final_content = result.params.get("content", content)
+                final_team = result.params.get("team_id", team_id)
+                final_channel = result.params.get("channel_id", channel_id)
+
+                token = await get_access_token(db_session, connector)
+
+                async with httpx.AsyncClient(timeout=20.0) as client:
+                    resp = await client.post(
+                        f"{GRAPH_API}/teams/{final_team}/channels/{final_channel}/messages",
+                        headers={
+                            "Authorization": f"Bearer {token}",
+                            "Content-Type": "application/json",
+                        },
+                        json={"body": {"content": final_content}},
+                    )
+
+                if resp.status_code == 401:
+                    return {
+                        "status": "auth_error",
+                        "message": "Teams token expired. Please re-authenticate.",
+                        "connector_type": "teams",
+                    }
+                if resp.status_code == 403:
+                    return {
+                        "status": "insufficient_permissions",
+                        "message": "Missing ChannelMessage.Send permission. Please re-authenticate with updated scopes.",
+                    }
+                if resp.status_code not in (200, 201):
+                    return {
+                        "status": "error",
+                        "message": f"Graph API error: {resp.status_code} — {resp.text[:200]}",
+                    }
+
+                msg_data = resp.json()
+                return {
+                    "status": "success",
+                    "message_id": msg_data.get("id"),
+                    "message": "Message sent to Teams channel.",
+                }
 
         except Exception as e:
             from langgraph.errors import GraphInterrupt

surfsense_backend/app/agents/new_chat/tools/update_memory.py

@@ -26,7 +26,7 @@ from langchain_core.tools import tool
 from sqlalchemy import select
 from sqlalchemy.ext.asyncio import AsyncSession
 
-from app.db import SearchSpace, User
+from app.db import SearchSpace, User, async_session_maker
 
 logger = logging.getLogger(__name__)
 
@@ -295,6 +295,25 @@ def create_update_memory_tool(
     db_session: AsyncSession,
     llm: Any | None = None,
 ):
+    """Factory function to create the user-memory update tool.
+
+    The tool acquires its own short-lived ``AsyncSession`` per call via
+    :data:`async_session_maker` so the closure is safe to share across
+    HTTP requests by the compiled-agent cache. Capturing a per-request
+    session here would surface stale/closed sessions on cache hits.
+    The session's bound ``commit``/``rollback`` methods are captured at
+    call time, after ``async with`` has bound ``db_session`` locally.
+
+    Args:
+        user_id: ID of the user whose memory document is being updated.
+        db_session: Reserved for registry compatibility. Per-call sessions
+            are opened via :data:`async_session_maker` inside the tool body.
+        llm: Optional LLM for the forced-rewrite path.
+
+    Returns:
+        Configured update_memory tool for the user-memory scope.
+    """
+    del db_session  # per-call session — see docstring
     uid = UUID(user_id) if isinstance(user_id, str) else user_id
 
     @tool
@@ -311,26 +330,26 @@ def create_update_memory_tool(
             updated_memory: The FULL updated markdown document (not a diff).
         """
         try:
-            result = await db_session.execute(select(User).where(User.id == uid))
-            user = result.scalars().first()
-            if not user:
-                return {"status": "error", "message": "User not found."}
+            async with async_session_maker() as db_session:
+                result = await db_session.execute(select(User).where(User.id == uid))
+                user = result.scalars().first()
+                if not user:
+                    return {"status": "error", "message": "User not found."}
 
-            old_memory = user.memory_md
+                old_memory = user.memory_md
 
-            return await _save_memory(
-                updated_memory=updated_memory,
-                old_memory=old_memory,
-                llm=llm,
-                apply_fn=lambda content: setattr(user, "memory_md", content),
-                commit_fn=db_session.commit,
-                rollback_fn=db_session.rollback,
-                label="memory",
-                scope="user",
-            )
+                return await _save_memory(
+                    updated_memory=updated_memory,
+                    old_memory=old_memory,
+                    llm=llm,
+                    apply_fn=lambda content: setattr(user, "memory_md", content),
+                    commit_fn=db_session.commit,
+                    rollback_fn=db_session.rollback,
+                    label="memory",
+                    scope="user",
+                )
         except Exception as e:
             logger.exception("Failed to update user memory: %s", e)
-            await db_session.rollback()
             return {
                 "status": "error",
                 "message": f"Failed to update memory: {e}",
@@ -344,6 +363,27 @@ def create_update_team_memory_tool(
     db_session: AsyncSession,
     llm: Any | None = None,
 ):
+    """Factory function to create the team-memory update tool.
+
+    The tool acquires its own short-lived ``AsyncSession`` per call via
+    :data:`async_session_maker` so the closure is safe to share across
+    HTTP requests by the compiled-agent cache. Capturing a per-request
+    session here would surface stale/closed sessions on cache hits.
+    The session's bound ``commit``/``rollback`` methods are captured at
+    call time, after ``async with`` has bound ``db_session`` locally.
+
+    Args:
+        search_space_id: ID of the search space whose team memory is being
+            updated.
+        db_session: Reserved for registry compatibility. Per-call sessions
+            are opened via :data:`async_session_maker` inside the tool body.
+        llm: Optional LLM for the forced-rewrite path.
+
+    Returns:
+        Configured update_memory tool for the team-memory scope.
+    """
+    del db_session  # per-call session — see docstring
+
     @tool
     async def update_memory(updated_memory: str) -> dict[str, Any]:
         """Update the team's shared memory document for this search space.
@@ -359,28 +399,30 @@ def create_update_team_memory_tool(
             updated_memory: The FULL updated markdown document (not a diff).
         """
         try:
-            result = await db_session.execute(
-                select(SearchSpace).where(SearchSpace.id == search_space_id)
-            )
-            space = result.scalars().first()
-            if not space:
-                return {"status": "error", "message": "Search space not found."}
+            async with async_session_maker() as db_session:
+                result = await db_session.execute(
+                    select(SearchSpace).where(SearchSpace.id == search_space_id)
+                )
+                space = result.scalars().first()
+                if not space:
+                    return {"status": "error", "message": "Search space not found."}
 
-            old_memory = space.shared_memory_md
+                old_memory = space.shared_memory_md
 
-            return await _save_memory(
-                updated_memory=updated_memory,
-                old_memory=old_memory,
-                llm=llm,
-                apply_fn=lambda content: setattr(space, "shared_memory_md", content),
-                commit_fn=db_session.commit,
-                rollback_fn=db_session.rollback,
-                label="team memory",
-                scope="team",
-            )
+                return await _save_memory(
+                    updated_memory=updated_memory,
+                    old_memory=old_memory,
+                    llm=llm,
+                    apply_fn=lambda content: setattr(
+                        space, "shared_memory_md", content
+                    ),
+                    commit_fn=db_session.commit,
+                    rollback_fn=db_session.rollback,
+                    label="team memory",
+                    scope="team",
+                )
         except Exception as e:
             logger.exception("Failed to update team memory: %s", e)
-            await db_session.rollback()
             return {
                 "status": "error",
                 "message": f"Failed to update team memory: {e}",

surfsense_backend/app/app.py

@@ -421,6 +421,135 @@ def _stop_openrouter_background_refresh() -> None:
         OpenRouterIntegrationService.get_instance().stop_background_refresh()
 
 
+async def _warm_agent_jit_caches() -> None:
+    """Pay the LangChain / LangGraph / Deepagents JIT cost at startup.
+
+    Why
+    ----
+    A cold ``create_agent`` + ``StateGraph.compile()`` + Pydantic schema
+    generation chain takes 1.5-2 seconds of pure CPU on first invocation
+    inside any Python process: the graph compiler builds reducers,
+    Pydantic v2 generates and JITs validator schemas, deepagents
+    eagerly compiles its general-purpose subagent, etc. Subsequent
+    compiles in the same process pay only ~50% of that cost (the lazy
+    JIT bits are cached in module-level dicts).
+
+    Doing one throwaway compile during ``lifespan`` startup pre-pays
+    that cost so the *first real request* doesn't. We do NOT prime
+    :mod:`agent_cache` because the cache key requires real
+    ``thread_id`` / ``user_id`` / ``search_space_id`` / etc. — the
+    throwaway agent is genuinely thrown away and immediately collected.
+
+    Safety
+    ------
+    * No DB access. We construct a stub LLM (no real keys), pass an
+      empty tools list, and pass ``checkpointer=None`` so we never
+      touch Postgres.
+    * Bounded by ``asyncio.wait_for`` so a hang here can never block
+      worker startup. On any failure, we log + swallow — the worst
+      case is the first real request pays the full cold cost (i.e.
+      pre-warmup behaviour).
+    """
+    import time as _time
+
+    logger = logging.getLogger(__name__)
+    t0 = _time.perf_counter()
+    try:
+        from langchain.agents import create_agent
+        from langchain.agents.middleware import (
+            ModelCallLimitMiddleware,
+            TodoListMiddleware,
+            ToolCallLimitMiddleware,
+        )
+        from langchain_core.language_models.fake_chat_models import (
+            FakeListChatModel,
+        )
+        from langchain_core.tools import tool
+
+        from app.agents.new_chat.context import SurfSenseContextSchema
+
+        # Minimal LLM stub. ``FakeListChatModel`` satisfies
+        # ``BaseChatModel`` without any network or auth — perfect for
+        # exercising the compile path without side effects.
+        stub_llm = FakeListChatModel(responses=["warmup-response"])
+
+        # Two trivial tools with arg + return schemas — exercises the
+        # Pydantic v2 schema JIT path. Without at least one tool the
+        # graph compile skips the tool-loop bytecode generation that
+        # accounts for ~30-50% of cold compile cost.
+        @tool
+        def _warmup_tool_a(query: str, limit: int = 5) -> str:
+            """Warmup tool A — never actually invoked."""
+            return query[:limit]
+
+        @tool
+        def _warmup_tool_b(name: str, value: float | None = None) -> dict[str, object]:
+            """Warmup tool B — never actually invoked."""
+            return {"name": name, "value": value}
+
+        # A handful of common middleware so the compile pre-pays the
+        # ``AgentMiddleware`` resolver path. These instances never run
+        # because the throwaway agent is immediately collected.
+        # ``SubAgentMiddleware`` is the single heaviest line in cold
+        # ``create_surfsense_deep_agent`` (1.5-2s of CPU per call to
+        # compile its general-purpose subagent's full inner graph),
+        # so we include it here to make sure that compile path is JIT'd.
+        warmup_middleware: list = [
+            TodoListMiddleware(),
+            ModelCallLimitMiddleware(
+                thread_limit=120, run_limit=80, exit_behavior="end"
+            ),
+            ToolCallLimitMiddleware(
+                thread_limit=300, run_limit=80, exit_behavior="continue"
+            ),
+        ]
+        try:
+            from deepagents import SubAgentMiddleware
+            from deepagents.backends import StateBackend
+            from deepagents.middleware.subagents import GENERAL_PURPOSE_SUBAGENT
+
+            gp_warmup_spec = {  # type: ignore[var-annotated]
+                **GENERAL_PURPOSE_SUBAGENT,
+                "model": stub_llm,
+                "tools": [_warmup_tool_a],
+                "middleware": [TodoListMiddleware()],
+            }
+            warmup_middleware.append(
+                SubAgentMiddleware(backend=StateBackend, subagents=[gp_warmup_spec])
+            )
+        except Exception:
+            # Deepagents missing/incompatible — middleware-only warmup
+            # still produces a useful (smaller) speedup.
+            logger.debug("[startup] SubAgentMiddleware warmup skipped", exc_info=True)
+
+        compiled = create_agent(
+            stub_llm,
+            tools=[_warmup_tool_a, _warmup_tool_b],
+            system_prompt="You are a warmup stub.",
+            middleware=warmup_middleware,
+            context_schema=SurfSenseContextSchema,
+            checkpointer=None,
+        )
+
+        # Touch the compiled graph's stream_channels / nodes so any
+        # remaining lazy schema work fires now instead of on first
+        # real invocation.
+        _ = list(getattr(compiled, "nodes", {}).keys())
+
+        del compiled
+        logger.info(
+            "[startup] Agent JIT warmup completed in %.3fs",
+            _time.perf_counter() - t0,
+        )
+    except Exception:
+        logger.warning(
+            "[startup] Agent JIT warmup failed in %.3fs (non-fatal — first "
+            "real request will pay the full compile cost)",
+            _time.perf_counter() - t0,
+            exc_info=True,
+        )
+
+
 @asynccontextmanager
 async def lifespan(app: FastAPI):
     # Tune GC: lower gen-2 threshold so long-lived garbage is collected
@@ -445,6 +574,18 @@ async def lifespan(app: FastAPI):
             "Docs will be indexed on the next restart."
         )
 
+    # Phase 1.7 — JIT warmup. Bounded so a stuck warmup never delays
+    # worker readiness. ``shield`` so Uvicorn cancelling startup
+    # doesn't leave half-warmed Pydantic schemas in an inconsistent
+    # state.
+    try:
+        await asyncio.wait_for(asyncio.shield(_warm_agent_jit_caches()), timeout=20)
+    except (TimeoutError, Exception):  # pragma: no cover - defensive
+        logging.getLogger(__name__).warning(
+            "[startup] Agent JIT warmup hit timeout/error — skipping; "
+            "first real request will pay the full compile cost."
+        )
+
     log_system_snapshot("startup_complete")
 
     yield

surfsense_backend/app/services/connector_service.py

@@ -1,6 +1,8 @@
 import asyncio
+import os
 import time
 from datetime import datetime
+from threading import Lock
 from typing import Any
 
 import httpx
@@ -2769,12 +2771,22 @@ class ConnectorService:
         """
         Get all available (enabled) connector types for a search space.
 
+        Phase 1.4: results are cached per ``search_space_id`` for
+        :data:`_DISCOVERY_TTL_SECONDS`. Cache key is independent of session
+        identity — the cached value is plain data, safe to share across
+        requests. Invalidate on connector add/update/delete via
+        :func:`invalidate_connector_discovery_cache`.
+
         Args:
             search_space_id: The search space ID
 
         Returns:
             List of SearchSourceConnectorType enums for enabled connectors
         """
+        cached = _get_cached_connectors(search_space_id)
+        if cached is not None:
+            return list(cached)
+
         query = (
             select(SearchSourceConnector.connector_type)
             .filter(
@@ -2784,8 +2796,9 @@ class ConnectorService:
         )
 
         result = await self.session.execute(query)
-        connector_types = result.scalars().all()
-        return list(connector_types)
+        connector_types = list(result.scalars().all())
+        _set_cached_connectors(search_space_id, connector_types)
+        return connector_types
 
     async def get_available_document_types(
         self,
@@ -2794,12 +2807,22 @@ class ConnectorService:
         """
         Get all document types that have at least one document in the search space.
 
+        Phase 1.4: cached per ``search_space_id`` for
+        :data:`_DISCOVERY_TTL_SECONDS`. Invalidate via
+        :func:`invalidate_connector_discovery_cache` when a connector
+        finishes indexing new documents (or document types are otherwise
+        added/removed).
+
         Args:
             search_space_id: The search space ID
 
         Returns:
             List of document type strings that have documents indexed
         """
+        cached = _get_cached_doc_types(search_space_id)
+        if cached is not None:
+            return list(cached)
+
         from sqlalchemy import distinct
 
         from app.db import Document
@@ -2809,5 +2832,164 @@ class ConnectorService:
         )
 
         result = await self.session.execute(query)
-        doc_types = result.scalars().all()
-        return [str(dt) for dt in doc_types]
+        doc_types = [str(dt) for dt in result.scalars().all()]
+        _set_cached_doc_types(search_space_id, doc_types)
+        return doc_types
+
+
+# ---------------------------------------------------------------------------
+# Connector / document-type discovery TTL cache (Phase 1.4)
+# ---------------------------------------------------------------------------
+#
+# Both ``get_available_connectors`` and ``get_available_document_types`` are
+# called on EVERY chat turn from ``create_surfsense_deep_agent``. Each query
+# hits Postgres and contributes to per-turn agent build latency. Their
+# results change infrequently — only when the user adds/edits/removes a
+# connector, or when an indexer commits a new document type. A short TTL
+# cache (default 30s, env-tunable) collapses N concurrent calls into one
+# DB roundtrip with bounded staleness.
+#
+# Invalidation: connector mutation routes (create / update / delete) call
+# ``invalidate_connector_discovery_cache(search_space_id)`` to clear the
+# entry for the affected space. Multi-replica deployments still pay one
+# DB roundtrip per replica per TTL window, which is fine — staleness is
+# bounded and the alternative (cross-replica fanout) is not worth the
+# coupling here.
+
+_DISCOVERY_TTL_SECONDS: float = float(
+    os.getenv("SURFSENSE_CONNECTOR_DISCOVERY_TTL_SECONDS", "30")
+)
+
+# Per-search-space caches. Keyed by ``search_space_id``; value is
+# ``(expires_at_monotonic, payload)``. Plain dicts protected by a lock —
+# read-mostly workload, sub-microsecond contention.
+_connectors_cache: dict[int, tuple[float, list[SearchSourceConnectorType]]] = {}
+_doc_types_cache: dict[int, tuple[float, list[str]]] = {}
+_cache_lock = Lock()
+
+
+def _get_cached_connectors(
+    search_space_id: int,
+) -> list[SearchSourceConnectorType] | None:
+    if _DISCOVERY_TTL_SECONDS <= 0:
+        return None
+    with _cache_lock:
+        entry = _connectors_cache.get(search_space_id)
+        if entry is None:
+            return None
+        expires_at, payload = entry
+        if time.monotonic() >= expires_at:
+            _connectors_cache.pop(search_space_id, None)
+            return None
+        return payload
+
+
+def _set_cached_connectors(
+    search_space_id: int, payload: list[SearchSourceConnectorType]
+) -> None:
+    if _DISCOVERY_TTL_SECONDS <= 0:
+        return
+    expires_at = time.monotonic() + _DISCOVERY_TTL_SECONDS
+    with _cache_lock:
+        _connectors_cache[search_space_id] = (expires_at, list(payload))
+
+
+def _get_cached_doc_types(search_space_id: int) -> list[str] | None:
+    if _DISCOVERY_TTL_SECONDS <= 0:
+        return None
+    with _cache_lock:
+        entry = _doc_types_cache.get(search_space_id)
+        if entry is None:
+            return None
+        expires_at, payload = entry
+        if time.monotonic() >= expires_at:
+            _doc_types_cache.pop(search_space_id, None)
+            return None
+        return payload
+
+
+def _set_cached_doc_types(search_space_id: int, payload: list[str]) -> None:
+    if _DISCOVERY_TTL_SECONDS <= 0:
+        return
+    expires_at = time.monotonic() + _DISCOVERY_TTL_SECONDS
+    with _cache_lock:
+        _doc_types_cache[search_space_id] = (expires_at, list(payload))
+
+
+def invalidate_connector_discovery_cache(search_space_id: int | None = None) -> None:
+    """Drop cached discovery results for ``search_space_id`` (or all spaces).
+
+    Connector CRUD routes / indexer pipelines call this when they mutate
+    the rows backing :func:`ConnectorService.get_available_connectors` /
+    :func:`get_available_document_types`. ``None`` clears every space —
+    useful in tests and on bulk imports.
+    """
+    with _cache_lock:
+        if search_space_id is None:
+            _connectors_cache.clear()
+            _doc_types_cache.clear()
+        else:
+            _connectors_cache.pop(search_space_id, None)
+            _doc_types_cache.pop(search_space_id, None)
+
+
+def _invalidate_connectors_only(search_space_id: int | None = None) -> None:
+    with _cache_lock:
+        if search_space_id is None:
+            _connectors_cache.clear()
+        else:
+            _connectors_cache.pop(search_space_id, None)
+
+
+def _invalidate_doc_types_only(search_space_id: int | None = None) -> None:
+    with _cache_lock:
+        if search_space_id is None:
+            _doc_types_cache.clear()
+        else:
+            _doc_types_cache.pop(search_space_id, None)
+
+
+def _register_invalidation_listeners() -> None:
+    """Wire SQLAlchemy ORM events so cache stays consistent automatically.
+
+    Listening on ``after_insert`` / ``after_update`` / ``after_delete``
+    means every successful INSERT/UPDATE/DELETE that goes through the ORM
+    invalidates the affected search space's cached discovery payload —
+    no need to sprinkle ``invalidate_*`` calls across 30+ connector
+    routes. Bulk operations that bypass the ORM (e.g.
+    ``session.execute(insert(...))`` without a mapped object) still need
+    explicit invalidation; document indexers already commit through the
+    ORM so document-type discovery is covered.
+    """
+    from sqlalchemy import event
+
+    # Imported here (not at module top) to avoid a circular import:
+    # app.services.connector_service is itself imported from app.db's
+    # ecosystem indirectly via several CRUD modules.
+    from app.db import Document, SearchSourceConnector
+
+    def _connector_changed(_mapper, _connection, target) -> None:
+        sid = getattr(target, "search_space_id", None)
+        if sid is not None:
+            _invalidate_connectors_only(int(sid))
+
+    def _document_changed(_mapper, _connection, target) -> None:
+        sid = getattr(target, "search_space_id", None)
+        if sid is not None:
+            _invalidate_doc_types_only(int(sid))
+
+    for evt in ("after_insert", "after_update", "after_delete"):
+        event.listen(SearchSourceConnector, evt, _connector_changed)
+        event.listen(Document, evt, _document_changed)
+
+
+try:
+    _register_invalidation_listeners()
+except Exception:  # pragma: no cover - defensive; never block module import
+    import logging as _logging
+
+    _logging.getLogger(__name__).exception(
+        "Failed to register connector discovery cache invalidation listeners; "
+        "stale cache risk: explicit invalidate_connector_discovery_cache calls "
+        "may be required."
+    )

surfsense_backend/app/tasks/chat/stream_new_chat.py

@@ -31,6 +31,7 @@ from sqlalchemy.orm import selectinload
 
 from app.agents.new_chat.chat_deepagent import create_surfsense_deep_agent
 from app.agents.new_chat.checkpointer import get_checkpointer
+from app.agents.new_chat.context import SurfSenseContextSchema
 from app.agents.new_chat.errors import BusyError
 from app.agents.new_chat.feature_flags import get_flags
 from app.agents.new_chat.filesystem_selection import FilesystemMode, FilesystemSelection
@@ -559,6 +560,29 @@ async def _preflight_llm(llm: Any) -> None:
         )
 
 
+async def _settle_speculative_agent_build(task: asyncio.Task[Any]) -> None:
+    """Wait for a discarded speculative agent build to release shared state.
+
+    Used by the parallel preflight + agent-build path. The speculative build
+    closes over the request-scoped ``AsyncSession`` (for the brief connector
+    discovery / tool-factory window before its CPU work moves into a worker
+    thread). If preflight reports a 429 we want to fall back to the original
+    repin → reload → rebuild path, but we MUST NOT touch ``session`` again
+    until any in-flight session work owned by the speculative build has
+    fully settled — :class:`sqlalchemy.ext.asyncio.AsyncSession` is not
+    concurrency-safe and the same hazard cost us a hard ``InvalidRequestError``
+    earlier in this PR (see ``connector_service`` parallel-gather revert).
+
+    We simply ``await`` the task and swallow any exception: in this path the
+    build's outcome is irrelevant — success populates the agent cache (a free
+    side effect), failure is discarded. The wasted CPU is acceptable since
+    429 fallbacks are rare and the original sequential code also paid the
+    full build cost on the same path.
+    """
+    with contextlib.suppress(BaseException):
+        await task
+
+
 def _classify_stream_exception(
     exc: Exception,
     *,
@@ -696,6 +720,7 @@ async def _stream_agent_events(
     fallback_commit_created_by_id: str | None = None,
     fallback_commit_filesystem_mode: FilesystemMode = FilesystemMode.CLOUD,
     fallback_commit_thread_id: int | None = None,
+    runtime_context: Any = None,
 ) -> AsyncGenerator[str, None]:
     """Shared async generator that streams and formats astream_events from the agent.
 
@@ -801,7 +826,18 @@ async def _stream_agent_events(
             return event
         return None
 
-    async for event in agent.astream_events(input_data, config=config, version="v2"):
+    # Per-invocation runtime context (Phase 1.5). When supplied,
+    # ``KnowledgePriorityMiddleware`` reads ``mentioned_document_ids``
+    # from ``runtime.context`` instead of its constructor closure — the
+    # prerequisite that lets the compiled-agent cache (Phase 1) reuse a
+    # single graph across turns. Astream_events_kwargs stays empty when
+    # callers leave ``runtime_context`` as ``None`` to preserve the
+    # legacy code path bit-for-bit.
+    astream_kwargs: dict[str, Any] = {"config": config, "version": "v2"}
+    if runtime_context is not None:
+        astream_kwargs["context"] = runtime_context
+
+    async for event in agent.astream_events(input_data, **astream_kwargs):
         event_type = event.get("event", "")
 
         if event_type == "on_chat_model_stream":
@@ -2560,23 +2596,102 @@ async def stream_new_chat(
         # Detecting a 429 here lets us repin BEFORE the planner/classifier/
         # title-generation LLM calls fan out and each independently hit the
         # same upstream rate limit.
-        if (
+        #
+        # PERF: preflight is a network round-trip to the LLM provider (~1-5s)
+        # and is independent of the agent build (CPU-bound, ~5-7s). They used
+        # to run sequentially → ``preflight + build`` on cold cache = 11.5s.
+        # We now kick off preflight as a background task FIRST, then run the
+        # synchronous setup work and the agent build in parallel. In the
+        # success path (the common case) total wall time drops to roughly
+        # ``max(preflight, build)`` — the preflight finishes during the
+        # agent compile and we just consume its result. In the rare 429
+        # path the speculative build is awaited to completion (so its
+        # session usage is fully released) via
+        # :func:`_settle_speculative_agent_build`, then discarded, and
+        # we fall back to the original repin-and-rebuild flow.
+        preflight_needed = (
             requested_llm_config_id == 0
             and llm_config_id < 0
             and not is_recently_healthy(llm_config_id)
-        ):
+        )
+        preflight_task: asyncio.Task[None] | None = None
+        _t_preflight = 0.0
+        if preflight_needed:
             _t_preflight = time.perf_counter()
+            preflight_task = asyncio.create_task(
+                _preflight_llm(llm),
+                name=f"auto_pin_preflight:{llm_config_id}",
+            )
+
+        # Create connector service
+        _t0 = time.perf_counter()
+        connector_service = ConnectorService(session, search_space_id=search_space_id)
+
+        firecrawl_api_key = None
+        webcrawler_connector = await connector_service.get_connector_by_type(
+            SearchSourceConnectorType.WEBCRAWLER_CONNECTOR, search_space_id
+        )
+        if webcrawler_connector and webcrawler_connector.config:
+            firecrawl_api_key = webcrawler_connector.config.get("FIRECRAWL_API_KEY")
+        _perf_log.info(
+            "[stream_new_chat] Connector service + firecrawl key in %.3fs",
+            time.perf_counter() - _t0,
+        )
+
+        # Get the PostgreSQL checkpointer for persistent conversation memory
+        _t0 = time.perf_counter()
+        checkpointer = await get_checkpointer()
+        _perf_log.info(
+            "[stream_new_chat] Checkpointer ready in %.3fs", time.perf_counter() - _t0
+        )
+
+        visibility = thread_visibility or ChatVisibility.PRIVATE
+        _t0 = time.perf_counter()
+        # Speculative agent build — runs in parallel with the preflight
+        # task (if any). Built with the *current* ``llm`` / ``agent_config``;
+        # if preflight reports 429 we will discard this future and rebuild
+        # against the freshly pinned config below.
+        agent_build_task = asyncio.create_task(
+            create_surfsense_deep_agent(
+                llm=llm,
+                search_space_id=search_space_id,
+                db_session=session,
+                connector_service=connector_service,
+                checkpointer=checkpointer,
+                user_id=user_id,
+                thread_id=chat_id,
+                agent_config=agent_config,
+                firecrawl_api_key=firecrawl_api_key,
+                thread_visibility=visibility,
+                disabled_tools=disabled_tools,
+                mentioned_document_ids=mentioned_document_ids,
+                filesystem_selection=filesystem_selection,
+            ),
+            name="agent_build:stream_new_chat",
+        )
+
+        agent: Any = None
+        if preflight_task is not None:
             try:
-                await _preflight_llm(llm)
+                await preflight_task
                 mark_healthy(llm_config_id)
                 _perf_log.info(
-                    "[stream_new_chat] auto_pin_preflight ok config_id=%s took=%.3fs",
+                    "[stream_new_chat] auto_pin_preflight ok config_id=%s took=%.3fs (parallel)",
                     llm_config_id,
                     time.perf_counter() - _t_preflight,
                 )
             except Exception as preflight_exc:
+                # Both branches below need the session: the non-429 path
+                # may unwind via cleanup that uses ``session``, and the
+                # 429 path explicitly calls ``resolve_or_get_pinned_llm_config_id``
+                # against it. Wait for the speculative build to release its
+                # session usage before we proceed.
+                await _settle_speculative_agent_build(agent_build_task)
                 if not _is_provider_rate_limited(preflight_exc):
                     raise
+                # 429: speculative agent is discarded; run the original
+                # repin → reload → rebuild path against the freshly
+                # pinned config.
                 previous_config_id = llm_config_id
                 mark_runtime_cooldown(
                     previous_config_id, reason="preflight_rate_limited"
@@ -2639,46 +2754,28 @@ async def stream_new_chat(
                         "fallback_config_id": llm_config_id,
                     },
                 )
+                # Rebuild against the new llm/agent_config. Sequential
+                # here because we no longer have anything to overlap with.
+                agent = await create_surfsense_deep_agent(
+                    llm=llm,
+                    search_space_id=search_space_id,
+                    db_session=session,
+                    connector_service=connector_service,
+                    checkpointer=checkpointer,
+                    user_id=user_id,
+                    thread_id=chat_id,
+                    agent_config=agent_config,
+                    firecrawl_api_key=firecrawl_api_key,
+                    thread_visibility=visibility,
+                    disabled_tools=disabled_tools,
+                    mentioned_document_ids=mentioned_document_ids,
+                    filesystem_selection=filesystem_selection,
+                )
 
-        # Create connector service
-        _t0 = time.perf_counter()
-        connector_service = ConnectorService(session, search_space_id=search_space_id)
-
-        firecrawl_api_key = None
-        webcrawler_connector = await connector_service.get_connector_by_type(
-            SearchSourceConnectorType.WEBCRAWLER_CONNECTOR, search_space_id
-        )
-        if webcrawler_connector and webcrawler_connector.config:
-            firecrawl_api_key = webcrawler_connector.config.get("FIRECRAWL_API_KEY")
-        _perf_log.info(
-            "[stream_new_chat] Connector service + firecrawl key in %.3fs",
-            time.perf_counter() - _t0,
-        )
-
-        # Get the PostgreSQL checkpointer for persistent conversation memory
-        _t0 = time.perf_counter()
-        checkpointer = await get_checkpointer()
-        _perf_log.info(
-            "[stream_new_chat] Checkpointer ready in %.3fs", time.perf_counter() - _t0
-        )
-
-        visibility = thread_visibility or ChatVisibility.PRIVATE
-        _t0 = time.perf_counter()
-        agent = await create_surfsense_deep_agent(
-            llm=llm,
-            search_space_id=search_space_id,
-            db_session=session,
-            connector_service=connector_service,
-            checkpointer=checkpointer,
-            user_id=user_id,
-            thread_id=chat_id,
-            agent_config=agent_config,
-            firecrawl_api_key=firecrawl_api_key,
-            thread_visibility=visibility,
-            disabled_tools=disabled_tools,
-            mentioned_document_ids=mentioned_document_ids,
-            filesystem_selection=filesystem_selection,
-        )
+        if agent is None:
+            # Either no preflight was needed, or preflight succeeded —
+            # in both cases the speculative build is the agent we want.
+            agent = await agent_build_task
         _perf_log.info(
             "[stream_new_chat] Agent created in %.3fs", time.perf_counter() - _t0
         )
@@ -3005,6 +3102,18 @@ async def stream_new_chat(
 
         title_emitted = False
 
+        # Build the per-invocation runtime context (Phase 1.5).
+        # ``mentioned_document_ids`` is read by ``KnowledgePriorityMiddleware``
+        # via ``runtime.context.mentioned_document_ids`` instead of its
+        # ``__init__`` closure — that way the same compiled-agent instance
+        # can serve multiple turns with different mention lists.
+        runtime_context = SurfSenseContextSchema(
+            search_space_id=search_space_id,
+            mentioned_document_ids=list(mentioned_document_ids or []),
+            request_id=request_id,
+            turn_id=stream_result.turn_id,
+        )
+
         _t_stream_start = time.perf_counter()
         _first_event_logged = False
         runtime_rate_limit_recovered = False
@@ -3028,6 +3137,7 @@ async def stream_new_chat(
                         else FilesystemMode.CLOUD
                     ),
                     fallback_commit_thread_id=chat_id,
+                    runtime_context=runtime_context,
                 ):
                     if not _first_event_logged:
                         _perf_log.info(
@@ -3643,21 +3753,75 @@ async def stream_resume_chat(
         # Auto-mode preflight ping (resume path). Mirrors ``stream_new_chat``:
         # one cheap probe before the agent is rebuilt so a 429'd pin gets
         # repinned without burning planner/classifier/title calls first.
-        if (
+        # See ``stream_new_chat`` for the full rationale on the speculative
+        # parallel build pattern below.
+        preflight_needed = (
             requested_llm_config_id == 0
             and llm_config_id < 0
             and not is_recently_healthy(llm_config_id)
-        ):
+        )
+        preflight_task: asyncio.Task[None] | None = None
+        _t_preflight = 0.0
+        if preflight_needed:
             _t_preflight = time.perf_counter()
+            preflight_task = asyncio.create_task(
+                _preflight_llm(llm),
+                name=f"auto_pin_preflight_resume:{llm_config_id}",
+            )
+
+        _t0 = time.perf_counter()
+        connector_service = ConnectorService(session, search_space_id=search_space_id)
+
+        firecrawl_api_key = None
+        webcrawler_connector = await connector_service.get_connector_by_type(
+            SearchSourceConnectorType.WEBCRAWLER_CONNECTOR, search_space_id
+        )
+        if webcrawler_connector and webcrawler_connector.config:
+            firecrawl_api_key = webcrawler_connector.config.get("FIRECRAWL_API_KEY")
+        _perf_log.info(
+            "[stream_resume] Connector service + firecrawl key in %.3fs",
+            time.perf_counter() - _t0,
+        )
+
+        _t0 = time.perf_counter()
+        checkpointer = await get_checkpointer()
+        _perf_log.info(
+            "[stream_resume] Checkpointer ready in %.3fs", time.perf_counter() - _t0
+        )
+
+        visibility = thread_visibility or ChatVisibility.PRIVATE
+
+        _t0 = time.perf_counter()
+        agent_build_task = asyncio.create_task(
+            create_surfsense_deep_agent(
+                llm=llm,
+                search_space_id=search_space_id,
+                db_session=session,
+                connector_service=connector_service,
+                checkpointer=checkpointer,
+                user_id=user_id,
+                thread_id=chat_id,
+                agent_config=agent_config,
+                firecrawl_api_key=firecrawl_api_key,
+                thread_visibility=visibility,
+                filesystem_selection=filesystem_selection,
+            ),
+            name="agent_build:stream_resume",
+        )
+
+        agent: Any = None
+        if preflight_task is not None:
             try:
-                await _preflight_llm(llm)
+                await preflight_task
                 mark_healthy(llm_config_id)
                 _perf_log.info(
-                    "[stream_resume] auto_pin_preflight ok config_id=%s took=%.3fs",
+                    "[stream_resume] auto_pin_preflight ok config_id=%s took=%.3fs (parallel)",
                     llm_config_id,
                     time.perf_counter() - _t_preflight,
                 )
             except Exception as preflight_exc:
+                # Same session-safety rationale as ``stream_new_chat``.
+                await _settle_speculative_agent_build(agent_build_task)
                 if not _is_provider_rate_limited(preflight_exc):
                     raise
                 previous_config_id = llm_config_id
@@ -3717,43 +3881,22 @@ async def stream_resume_chat(
                         "fallback_config_id": llm_config_id,
                     },
                 )
+                agent = await create_surfsense_deep_agent(
+                    llm=llm,
+                    search_space_id=search_space_id,
+                    db_session=session,
+                    connector_service=connector_service,
+                    checkpointer=checkpointer,
+                    user_id=user_id,
+                    thread_id=chat_id,
+                    agent_config=agent_config,
+                    firecrawl_api_key=firecrawl_api_key,
+                    thread_visibility=visibility,
+                    filesystem_selection=filesystem_selection,
+                )
 
-        _t0 = time.perf_counter()
-        connector_service = ConnectorService(session, search_space_id=search_space_id)
-
-        firecrawl_api_key = None
-        webcrawler_connector = await connector_service.get_connector_by_type(
-            SearchSourceConnectorType.WEBCRAWLER_CONNECTOR, search_space_id
-        )
-        if webcrawler_connector and webcrawler_connector.config:
-            firecrawl_api_key = webcrawler_connector.config.get("FIRECRAWL_API_KEY")
-        _perf_log.info(
-            "[stream_resume] Connector service + firecrawl key in %.3fs",
-            time.perf_counter() - _t0,
-        )
-
-        _t0 = time.perf_counter()
-        checkpointer = await get_checkpointer()
-        _perf_log.info(
-            "[stream_resume] Checkpointer ready in %.3fs", time.perf_counter() - _t0
-        )
-
-        visibility = thread_visibility or ChatVisibility.PRIVATE
-
-        _t0 = time.perf_counter()
-        agent = await create_surfsense_deep_agent(
-            llm=llm,
-            search_space_id=search_space_id,
-            db_session=session,
-            connector_service=connector_service,
-            checkpointer=checkpointer,
-            user_id=user_id,
-            thread_id=chat_id,
-            agent_config=agent_config,
-            firecrawl_api_key=firecrawl_api_key,
-            thread_visibility=visibility,
-            filesystem_selection=filesystem_selection,
-        )
+        if agent is None:
+            agent = await agent_build_task
         _perf_log.info(
             "[stream_resume] Agent created in %.3fs", time.perf_counter() - _t0
         )
@@ -3794,6 +3937,16 @@ async def stream_resume_chat(
         )
         yield streaming_service.format_data("turn-status", {"status": "busy"})
 
+        # Resume path doesn't carry new ``mentioned_document_ids`` —
+        # those are seeded in the original turn. We still pass a
+        # context so future middleware extensions (Phase 2) can rely on
+        # ``runtime.context`` always being populated.
+        runtime_context = SurfSenseContextSchema(
+            search_space_id=search_space_id,
+            request_id=request_id,
+            turn_id=stream_result.turn_id,
+        )
+
         _t_stream_start = time.perf_counter()
         _first_event_logged = False
         runtime_rate_limit_recovered = False
@@ -3814,6 +3967,7 @@ async def stream_resume_chat(
                         else FilesystemMode.CLOUD
                     ),
                     fallback_commit_thread_id=chat_id,
+                    runtime_context=runtime_context,
                 ):
                     if not _first_event_logged:
                         _perf_log.info(

surfsense_backend/tests/unit/agents/new_chat/test_agent_cache.py

@@ -0,0 +1,268 @@
+"""Regression tests for the compiled-agent cache.
+
+Covers the cache primitive itself (TTL, LRU, in-flight de-duplication,
+build-failure non-caching) and the cache-key signature helpers that
+``create_surfsense_deep_agent`` relies on. The integration with
+``create_surfsense_deep_agent`` is covered separately by the streaming
+contract tests; this module focuses on the primitives so a regression
+in the cache implementation is caught before it reaches the agent
+factory.
+"""
+
+from __future__ import annotations
+
+import asyncio
+from dataclasses import dataclass
+
+import pytest
+
+from app.agents.new_chat.agent_cache import (
+    flags_signature,
+    reload_for_tests,
+    stable_hash,
+    system_prompt_hash,
+    tools_signature,
+)
+
+pytestmark = pytest.mark.unit
+
+
+# ---------------------------------------------------------------------------
+# stable_hash + signature helpers
+# ---------------------------------------------------------------------------
+
+
+def test_stable_hash_is_deterministic_across_calls() -> None:
+    a = stable_hash("v1", 42, "thread-9", None, ["x", "y"])
+    b = stable_hash("v1", 42, "thread-9", None, ["x", "y"])
+    assert a == b
+
+
+def test_stable_hash_changes_when_any_part_changes() -> None:
+    base = stable_hash("v1", 42, "thread-9")
+    assert stable_hash("v1", 42, "thread-10") != base
+    assert stable_hash("v2", 42, "thread-9") != base
+    assert stable_hash("v1", 43, "thread-9") != base
+
+
+def test_tools_signature_keys_on_name_and_description_not_identity() -> None:
+    """Two tool lists with the same surface must hash identically.
+
+    The cache key MUST NOT change when the underlying ``BaseTool``
+    instances are different Python objects (a fresh request constructs
+    fresh tool instances every time). Hashing on ``(name, description)``
+    keeps the cache hot across requests with identical tool surfaces.
+    """
+
+    @dataclass
+    class FakeTool:
+        name: str
+        description: str
+
+    tools_a = [FakeTool("alpha", "does alpha"), FakeTool("beta", "does beta")]
+    tools_b = [FakeTool("beta", "does beta"), FakeTool("alpha", "does alpha")]
+    sig_a = tools_signature(
+        tools_a, available_connectors=["NOTION"], available_document_types=["FILE"]
+    )
+    sig_b = tools_signature(
+        tools_b, available_connectors=["NOTION"], available_document_types=["FILE"]
+    )
+    assert sig_a == sig_b, "tool order must not affect the signature"
+
+    # Adding a tool rotates the key.
+    tools_c = [*tools_a, FakeTool("gamma", "does gamma")]
+    sig_c = tools_signature(
+        tools_c, available_connectors=["NOTION"], available_document_types=["FILE"]
+    )
+    assert sig_c != sig_a
+
+
+def test_tools_signature_rotates_when_connector_set_changes() -> None:
+    @dataclass
+    class FakeTool:
+        name: str
+        description: str
+
+    tools = [FakeTool("a", "x")]
+    base = tools_signature(
+        tools, available_connectors=["NOTION"], available_document_types=["FILE"]
+    )
+    added = tools_signature(
+        tools,
+        available_connectors=["NOTION", "SLACK"],
+        available_document_types=["FILE"],
+    )
+    assert base != added, "adding a connector must rotate the cache key"
+
+
+def test_flags_signature_changes_when_flag_flips() -> None:
+    @dataclass(frozen=True)
+    class Flags:
+        a: bool = True
+        b: bool = False
+
+    base = flags_signature(Flags())
+    flipped = flags_signature(Flags(b=True))
+    assert base != flipped
+
+
+def test_system_prompt_hash_is_stable_and_distinct() -> None:
+    p1 = "You are a helpful assistant."
+    p2 = "You are a helpful assistant!"  # one-character delta
+    assert system_prompt_hash(p1) == system_prompt_hash(p1)
+    assert system_prompt_hash(p1) != system_prompt_hash(p2)
+
+
+# ---------------------------------------------------------------------------
+# _AgentCache: hit / miss / TTL / LRU / coalescing / failure-not-cached
+# ---------------------------------------------------------------------------
+
+
+@pytest.mark.asyncio
+async def test_cache_hit_returns_same_instance_on_second_call() -> None:
+    cache = reload_for_tests(maxsize=8, ttl_seconds=60.0)
+    builds = 0
+
+    async def builder() -> object:
+        nonlocal builds
+        builds += 1
+        return object()
+
+    a = await cache.get_or_build("k", builder=builder)
+    b = await cache.get_or_build("k", builder=builder)
+    assert a is b, "cache must return the SAME object across hits"
+    assert builds == 1, "builder must run exactly once"
+
+
+@pytest.mark.asyncio
+async def test_cache_different_keys_get_different_instances() -> None:
+    cache = reload_for_tests(maxsize=8, ttl_seconds=60.0)
+
+    async def builder() -> object:
+        return object()
+
+    a = await cache.get_or_build("k1", builder=builder)
+    b = await cache.get_or_build("k2", builder=builder)
+    assert a is not b
+
+
+@pytest.mark.asyncio
+async def test_cache_stale_entries_get_rebuilt() -> None:
+    # ttl=0 means every read sees the entry as immediately stale.
+    cache = reload_for_tests(maxsize=8, ttl_seconds=0.0)
+    builds = 0
+
+    async def builder() -> object:
+        nonlocal builds
+        builds += 1
+        return object()
+
+    a = await cache.get_or_build("k", builder=builder)
+    b = await cache.get_or_build("k", builder=builder)
+    assert a is not b, "stale entry must rebuild a fresh instance"
+    assert builds == 2
+
+
+@pytest.mark.asyncio
+async def test_cache_evicts_lru_when_full() -> None:
+    cache = reload_for_tests(maxsize=2, ttl_seconds=60.0)
+
+    async def builder() -> object:
+        return object()
+
+    a = await cache.get_or_build("a", builder=builder)
+    _ = await cache.get_or_build("b", builder=builder)
+    # Re-touch "a" so "b" is now the LRU victim.
+    a_again = await cache.get_or_build("a", builder=builder)
+    assert a_again is a
+    # Inserting "c" should evict "b" (LRU), not "a".
+    _ = await cache.get_or_build("c", builder=builder)
+    assert cache.stats()["size"] == 2
+
+    # Confirm "a" is still hot (no rebuild) and "b" is gone (rebuild).
+    a_hit = await cache.get_or_build("a", builder=builder)
+    assert a_hit is a, "LRU must keep the most-recently-used 'a' entry"
+
+
+@pytest.mark.asyncio
+async def test_cache_concurrent_misses_coalesce_to_single_build() -> None:
+    """Two concurrent get_or_build calls on the same key must share one builder."""
+    cache = reload_for_tests(maxsize=8, ttl_seconds=60.0)
+    build_started = asyncio.Event()
+    builds = 0
+
+    async def slow_builder() -> object:
+        nonlocal builds
+        builds += 1
+        build_started.set()
+        # Yield control so the second waiter can race against us.
+        await asyncio.sleep(0.05)
+        return object()
+
+    task_a = asyncio.create_task(cache.get_or_build("k", builder=slow_builder))
+    # Wait until the first builder has started, then race a second waiter.
+    await build_started.wait()
+    task_b = asyncio.create_task(cache.get_or_build("k", builder=slow_builder))
+
+    a, b = await asyncio.gather(task_a, task_b)
+    assert a is b, "coalesced waiters must observe the same value"
+    assert builds == 1, "concurrent cold misses must collapse to ONE build"
+
+
+@pytest.mark.asyncio
+async def test_cache_does_not_store_failed_builds() -> None:
+    """A builder that raises must NOT poison the cache.
+
+    The next caller for the same key must run the builder again (not
+    re-raise the cached exception).
+    """
+    cache = reload_for_tests(maxsize=8, ttl_seconds=60.0)
+    attempts = 0
+
+    async def flaky_builder() -> object:
+        nonlocal attempts
+        attempts += 1
+        if attempts == 1:
+            raise RuntimeError("transient")
+        return object()
+
+    with pytest.raises(RuntimeError, match="transient"):
+        await cache.get_or_build("k", builder=flaky_builder)
+
+    # Second call must retry — not re-raise the cached exception.
+    value = await cache.get_or_build("k", builder=flaky_builder)
+    assert value is not None
+    assert attempts == 2
+
+
+@pytest.mark.asyncio
+async def test_cache_invalidate_drops_entry() -> None:
+    cache = reload_for_tests(maxsize=8, ttl_seconds=60.0)
+
+    async def builder() -> object:
+        return object()
+
+    a = await cache.get_or_build("k", builder=builder)
+    assert cache.invalidate("k") is True
+    b = await cache.get_or_build("k", builder=builder)
+    assert a is not b, "post-invalidation lookup must rebuild"
+
+
+@pytest.mark.asyncio
+async def test_cache_invalidate_prefix_drops_matching_entries() -> None:
+    cache = reload_for_tests(maxsize=16, ttl_seconds=60.0)
+
+    async def builder() -> object:
+        return object()
+
+    await cache.get_or_build("user:1:thread:1", builder=builder)
+    await cache.get_or_build("user:1:thread:2", builder=builder)
+    await cache.get_or_build("user:2:thread:1", builder=builder)
+
+    removed = cache.invalidate_prefix("user:1:")
+    assert removed == 2
+    assert cache.stats()["size"] == 1
+
+    # The user:2 entry must still be hot (no rebuild).
+    survivor_value = await cache.get_or_build("user:2:thread:1", builder=builder)
+    assert survivor_value is not None

surfsense_backend/tests/unit/agents/new_chat/test_feature_flags.py

@@ -34,6 +34,8 @@ def _clear_all(monkeypatch: pytest.MonkeyPatch) -> None:
         "SURFSENSE_ENABLE_STREAM_PARITY_V2",
         "SURFSENSE_ENABLE_PLUGIN_LOADER",
         "SURFSENSE_ENABLE_OTEL",
+        "SURFSENSE_ENABLE_AGENT_CACHE",
+        "SURFSENSE_ENABLE_AGENT_CACHE_SHARE_GP_SUBAGENT",
     ]:
         monkeypatch.delenv(name, raising=False)
 
@@ -62,6 +64,11 @@ def test_defaults_match_shipped_agent_stack(monkeypatch: pytest.MonkeyPatch) ->
     assert flags.enable_stream_parity_v2 is True
     assert flags.enable_plugin_loader is False
     assert flags.enable_otel is False
+    # Phase 2: agent cache is now default-on (the prerequisite tool
+    # ``db_session`` refactor landed). The companion gp-subagent share
+    # flag stays default-off pending data on cold-miss frequency.
+    assert flags.enable_agent_cache is True
+    assert flags.enable_agent_cache_share_gp_subagent is False
     assert flags.any_new_middleware_enabled() is True
 
 

surfsense_backend/tests/unit/agents/new_chat/test_flatten_system.py

@@ -0,0 +1,344 @@
+"""Tests for ``FlattenSystemMessageMiddleware``.
+
+The middleware exists to defend against Anthropic's "Found 5 cache_control
+blocks" 400 when our deepagent middleware stack stacks 5+ text blocks on
+the system message and the OpenRouter→Anthropic adapter redistributes
+``cache_control`` across all of them. The flattening collapses every
+all-text system content list to a single string before the LLM call.
+"""
+
+from __future__ import annotations
+
+from typing import Any
+from unittest.mock import MagicMock
+
+import pytest
+from langchain_core.messages import HumanMessage, SystemMessage
+
+from app.agents.new_chat.middleware.flatten_system import (
+    FlattenSystemMessageMiddleware,
+    _flatten_text_blocks,
+    _flattened_request,
+)
+
+pytestmark = pytest.mark.unit
+
+
+# ---------------------------------------------------------------------------
+# _flatten_text_blocks — pure helper, the heart of the middleware.
+# ---------------------------------------------------------------------------
+
+
+class TestFlattenTextBlocks:
+    def test_joins_text_blocks_with_double_newline(self) -> None:
+        blocks = [
+            {"type": "text", "text": "<surfsense base>"},
+            {"type": "text", "text": "<filesystem section>"},
+            {"type": "text", "text": "<skills section>"},
+        ]
+        assert (
+            _flatten_text_blocks(blocks)
+            == "<surfsense base>\n\n<filesystem section>\n\n<skills section>"
+        )
+
+    def test_handles_single_text_block(self) -> None:
+        blocks = [{"type": "text", "text": "only one"}]
+        assert _flatten_text_blocks(blocks) == "only one"
+
+    def test_handles_empty_list(self) -> None:
+        assert _flatten_text_blocks([]) == ""
+
+    def test_passes_through_bare_string_blocks(self) -> None:
+        # LangChain content can mix bare strings and dict blocks.
+        blocks = ["raw string", {"type": "text", "text": "dict block"}]
+        assert _flatten_text_blocks(blocks) == "raw string\n\ndict block"
+
+    def test_returns_none_for_image_block(self) -> None:
+        # System messages with images are rare — but we never want to
+        # silently lose the image payload by joining as text.
+        blocks = [
+            {"type": "text", "text": "look at this"},
+            {"type": "image_url", "image_url": {"url": "data:image/png..."}},
+        ]
+        assert _flatten_text_blocks(blocks) is None
+
+    def test_returns_none_for_non_dict_non_str_block(self) -> None:
+        blocks = [{"type": "text", "text": "hi"}, 42]  # type: ignore[list-item]
+        assert _flatten_text_blocks(blocks) is None
+
+    def test_returns_none_when_text_field_missing(self) -> None:
+        blocks = [{"type": "text"}]  # no ``text`` key
+        assert _flatten_text_blocks(blocks) is None
+
+    def test_returns_none_when_text_is_not_string(self) -> None:
+        blocks = [{"type": "text", "text": ["nested", "list"]}]
+        assert _flatten_text_blocks(blocks) is None
+
+    def test_drops_cache_control_from_inner_blocks(self) -> None:
+        # The whole point: existing cache_control on inner blocks is
+        # discarded so LiteLLM's ``cache_control_injection_points`` can
+        # re-attach exactly one breakpoint after flattening.
+        blocks = [
+            {"type": "text", "text": "first"},
+            {
+                "type": "text",
+                "text": "second",
+                "cache_control": {"type": "ephemeral"},
+            },
+        ]
+        flattened = _flatten_text_blocks(blocks)
+        assert flattened == "first\n\nsecond"
+        assert "cache_control" not in flattened  # type: ignore[operator]
+
+
+# ---------------------------------------------------------------------------
+# _flattened_request — decides when to override and when to no-op.
+# ---------------------------------------------------------------------------
+
+
+def _make_request(system_message: SystemMessage | None) -> Any:
+    """Build a minimal ModelRequest stub. We only need .system_message
+    and .override(system_message=...) — the middleware never touches
+    other fields.
+    """
+    request = MagicMock()
+    request.system_message = system_message
+
+    def override(**kwargs: Any) -> Any:
+        new_request = MagicMock()
+        new_request.system_message = kwargs.get(
+            "system_message", request.system_message
+        )
+        new_request.messages = kwargs.get("messages", getattr(request, "messages", []))
+        new_request.tools = kwargs.get("tools", getattr(request, "tools", []))
+        return new_request
+
+    request.override = override
+    return request
+
+
+class TestFlattenedRequest:
+    def test_collapses_multi_block_system_to_string(self) -> None:
+        sys = SystemMessage(
+            content=[
+                {"type": "text", "text": "<base>"},
+                {"type": "text", "text": "<todo>"},
+                {"type": "text", "text": "<filesystem>"},
+                {"type": "text", "text": "<skills>"},
+                {"type": "text", "text": "<subagents>"},
+            ]
+        )
+        request = _make_request(sys)
+        flattened = _flattened_request(request)
+
+        assert flattened is not None
+        assert isinstance(flattened.system_message, SystemMessage)
+        assert flattened.system_message.content == (
+            "<base>\n\n<todo>\n\n<filesystem>\n\n<skills>\n\n<subagents>"
+        )
+
+    def test_no_op_for_string_content(self) -> None:
+        sys = SystemMessage(content="already a string")
+        request = _make_request(sys)
+        assert _flattened_request(request) is None
+
+    def test_no_op_for_single_block_list(self) -> None:
+        # One block already produces one breakpoint — no need to flatten.
+        sys = SystemMessage(content=[{"type": "text", "text": "single"}])
+        request = _make_request(sys)
+        assert _flattened_request(request) is None
+
+    def test_no_op_when_system_message_missing(self) -> None:
+        request = _make_request(None)
+        assert _flattened_request(request) is None
+
+    def test_no_op_when_list_contains_non_text_block(self) -> None:
+        sys = SystemMessage(
+            content=[
+                {"type": "text", "text": "look"},
+                {"type": "image_url", "image_url": {"url": "data:..."}},
+            ]
+        )
+        request = _make_request(sys)
+        assert _flattened_request(request) is None
+
+    def test_preserves_additional_kwargs_and_metadata(self) -> None:
+        # Defensive: nothing in the current chain sets these on a system
+        # message, but losing them silently when something does in the
+        # future would be a regression. ``name`` in particular is the only
+        # ``additional_kwargs`` field that ChatLiteLLM's
+        # ``_convert_message_to_dict`` propagates onto the wire.
+        sys = SystemMessage(
+            content=[
+                {"type": "text", "text": "a"},
+                {"type": "text", "text": "b"},
+            ],
+            additional_kwargs={"name": "surfsense_system", "x": 1},
+            response_metadata={"tokens": 42},
+        )
+        sys.id = "sys-msg-1"
+        request = _make_request(sys)
+
+        flattened = _flattened_request(request)
+        assert flattened is not None
+        assert flattened.system_message.content == "a\n\nb"
+        assert flattened.system_message.additional_kwargs == {
+            "name": "surfsense_system",
+            "x": 1,
+        }
+        assert flattened.system_message.response_metadata == {"tokens": 42}
+        assert flattened.system_message.id == "sys-msg-1"
+
+    def test_idempotent_when_run_twice(self) -> None:
+        sys = SystemMessage(
+            content=[
+                {"type": "text", "text": "a"},
+                {"type": "text", "text": "b"},
+            ]
+        )
+        request = _make_request(sys)
+        first = _flattened_request(request)
+        assert first is not None
+
+        # Second pass on the already-flattened request should be a no-op.
+        # We re-wrap in a request stub since the helper inspects
+        # ``request.system_message.content``.
+        second_request = _make_request(first.system_message)
+        assert _flattened_request(second_request) is None
+
+
+# ---------------------------------------------------------------------------
+# Middleware integration — verify the handler sees a flattened request.
+# ---------------------------------------------------------------------------
+
+
+class TestMiddlewareWrap:
+    @pytest.mark.asyncio
+    async def test_async_passes_flattened_request_to_handler(self) -> None:
+        sys = SystemMessage(
+            content=[
+                {"type": "text", "text": "alpha"},
+                {"type": "text", "text": "beta"},
+            ]
+        )
+        request = _make_request(sys)
+        captured: dict[str, Any] = {}
+
+        async def handler(req: Any) -> str:
+            captured["request"] = req
+            return "ok"
+
+        mw = FlattenSystemMessageMiddleware()
+        result = await mw.awrap_model_call(request, handler)
+
+        assert result == "ok"
+        assert isinstance(captured["request"].system_message, SystemMessage)
+        assert captured["request"].system_message.content == "alpha\n\nbeta"
+
+    @pytest.mark.asyncio
+    async def test_async_passes_through_when_already_string(self) -> None:
+        sys = SystemMessage(content="just a string")
+        request = _make_request(sys)
+        captured: dict[str, Any] = {}
+
+        async def handler(req: Any) -> str:
+            captured["request"] = req
+            return "ok"
+
+        mw = FlattenSystemMessageMiddleware()
+        await mw.awrap_model_call(request, handler)
+
+        # Same request object: no override happened.
+        assert captured["request"] is request
+
+    def test_sync_passes_flattened_request_to_handler(self) -> None:
+        sys = SystemMessage(
+            content=[
+                {"type": "text", "text": "alpha"},
+                {"type": "text", "text": "beta"},
+            ]
+        )
+        request = _make_request(sys)
+        captured: dict[str, Any] = {}
+
+        def handler(req: Any) -> str:
+            captured["request"] = req
+            return "ok"
+
+        mw = FlattenSystemMessageMiddleware()
+        result = mw.wrap_model_call(request, handler)
+
+        assert result == "ok"
+        assert captured["request"].system_message.content == "alpha\n\nbeta"
+
+    def test_sync_passes_through_when_no_system_message(self) -> None:
+        request = _make_request(None)
+        captured: dict[str, Any] = {}
+
+        def handler(req: Any) -> str:
+            captured["request"] = req
+            return "ok"
+
+        mw = FlattenSystemMessageMiddleware()
+        mw.wrap_model_call(request, handler)
+        assert captured["request"] is request
+
+
+# ---------------------------------------------------------------------------
+# Regression guard — pin the worst-case shape that triggered the
+# "Found 5" 400 in production. Confirms we collapse 5 blocks to 1 so the
+# downstream cache_control_injection_points can only place 1 breakpoint
+# on the system message regardless of provider redistribution quirks.
+# ---------------------------------------------------------------------------
+
+
+def test_regression_five_block_system_collapses_to_one_block() -> None:
+    sys = SystemMessage(
+        content=[
+            {"type": "text", "text": "<surfsense base + BASE_AGENT_PROMPT>"},
+            {"type": "text", "text": "<TodoListMiddleware section>"},
+            {"type": "text", "text": "<SurfSenseFilesystemMiddleware section>"},
+            {"type": "text", "text": "<SkillsMiddleware section>"},
+            {"type": "text", "text": "<SubAgentMiddleware section>"},
+        ]
+    )
+    request = _make_request(sys)
+    flattened = _flattened_request(request)
+
+    assert flattened is not None
+    assert isinstance(flattened.system_message.content, str)
+    # The exact join doesn't matter for the cache_control accounting —
+    # only that there is exactly ONE content block when LiteLLM's
+    # AnthropicCacheControlHook later targets ``role: system``.
+    assert "<surfsense base" in flattened.system_message.content
+    assert "<SubAgentMiddleware" in flattened.system_message.content
+
+
+def test_regression_human_message_not_modified() -> None:
+    # Sanity: the middleware MUST NOT touch user messages — only the
+    # system message. Multi-block user content is the path that carries
+    # image attachments and would lose its image_url block on
+    # accidental flatten.
+    sys = SystemMessage(
+        content=[
+            {"type": "text", "text": "a"},
+            {"type": "text", "text": "b"},
+        ]
+    )
+    user = HumanMessage(
+        content=[
+            {"type": "text", "text": "look at this"},
+            {"type": "image_url", "image_url": {"url": "data:image/png;base64,..."}},
+        ]
+    )
+    request = _make_request(sys)
+    request.messages = [user]
+
+    flattened = _flattened_request(request)
+    assert flattened is not None
+    # System flattened to string …
+    assert isinstance(flattened.system_message.content, str)
+    # … user message is untouched (the helper does not even look at it).
+    assert flattened.messages == [user]
+    assert isinstance(user.content, list)
+    assert len(user.content) == 2

surfsense_backend/tests/unit/agents/new_chat/test_prompt_caching.py

@@ -1,4 +1,4 @@
-"""Tests for ``apply_litellm_prompt_caching`` in
+r"""Tests for ``apply_litellm_prompt_caching`` in
 :mod:`app.agents.new_chat.prompt_caching`.
 
 The helper replaces the legacy ``AnthropicPromptCachingMiddleware`` (which
@@ -6,9 +6,12 @@ never activated for our LiteLLM stack) with LiteLLM-native multi-provider
 prompt caching. It mutates ``llm.model_kwargs`` so the kwargs flow to
 ``litellm.completion(...)``. The tests below pin its public contract:
 
-1. Always sets BOTH ``role: system`` and ``index: -1`` injection points so
+1. Always sets BOTH ``index: 0`` and ``index: -1`` injection points so
    savings compound across multi-turn conversations on Anthropic-family
-   providers.
+   providers. ``index: 0`` is used (rather than ``role: system``) because
+   the deepagent stack accumulates multiple ``SystemMessage``\ s in
+   ``state["messages"]`` and ``role: system`` would tag every one of
+   them, blowing past Anthropic's 4-block ``cache_control`` cap.
 2. Adds ``prompt_cache_key``/``prompt_cache_retention`` only for
    single-model OPENAI/DEEPSEEK/XAI configs (where OpenAI's automatic
    prompt-cache surface is available).
@@ -92,11 +95,28 @@ def test_sets_both_cache_control_injection_points_with_no_config() -> None:
     apply_litellm_prompt_caching(llm)
 
     points = llm.model_kwargs["cache_control_injection_points"]
-    assert {"location": "message", "role": "system"} in points
+    assert {"location": "message", "index": 0} in points
     assert {"location": "message", "index": -1} in points
     assert len(points) == 2
 
 
+def test_does_not_inject_role_system_breakpoint() -> None:
+    """Regression: deliberately AVOID ``role: system`` so we don't tag
+    every SystemMessage the deepagent ``before_agent`` injectors push
+    into ``state["messages"]`` (priority, tree, memory, file-intent,
+    anonymous-doc). Tagging all of them overflows Anthropic's 4-block
+    ``cache_control`` cap and surfaces as
+    ``OpenrouterException: A maximum of 4 blocks with cache_control may
+    be provided. Found N`` 400s.
+    """
+    llm = _FakeLLM()
+    apply_litellm_prompt_caching(llm)
+    points = llm.model_kwargs["cache_control_injection_points"]
+    assert all(p.get("role") != "system" for p in points), (
+        f"Expected no role=system breakpoint, got: {points}"
+    )
+
+
 def test_injection_points_set_for_anthropic_config() -> None:
     """Anthropic-family configs need the marker — verify it lands."""
     cfg = _make_cfg(provider="ANTHROPIC", model_name="claude-3-5-sonnet")

surfsense_backend/tests/unit/middleware/test_knowledge_search.py

@@ -475,3 +475,190 @@ class TestKBSearchPlanSchema:
             )
         )
         assert plan.is_recency_query is False
+
+
+# ── mentioned_document_ids cross-turn drain ────────────────────────────
+
+
+class TestKnowledgePriorityMentionDrain:
+    """Regression tests for the cross-turn ``mentioned_document_ids`` drain.
+
+    The compiled-agent cache reuses a single :class:`KnowledgePriorityMiddleware`
+    instance across turns of the same thread. ``mentioned_document_ids``
+    can therefore enter the middleware via two paths:
+
+    1. The constructor closure (``__init__(mentioned_document_ids=...)``) —
+       seeded by the cache-miss build on turn 1.
+    2. ``runtime.context.mentioned_document_ids`` — supplied freshly per
+       turn by the streaming task.
+
+    Without the drain fix, an empty ``runtime.context.mentioned_document_ids``
+    on turn 2 would fall through to the closure (because ``[]`` is falsy in
+    Python) and replay turn 1's mentions. This class pins down the
+    correct behaviour: the runtime path is authoritative even when empty,
+    and the closure is drained the first time the runtime path fires so
+    no later turn can ever resurrect stale state.
+    """
+
+    @staticmethod
+    def _make_runtime(mention_ids: list[int]):
+        """Minimal runtime stub exposing only ``runtime.context.mentioned_document_ids``."""
+        from types import SimpleNamespace
+
+        return SimpleNamespace(
+            context=SimpleNamespace(mentioned_document_ids=mention_ids),
+        )
+
+    @staticmethod
+    def _planner_llm() -> "FakeLLM":
+        # Planner returns a stable, non-recency plan so we always land in
+        # the hybrid-search branch (where ``fetch_mentioned_documents`` is
+        # invoked alongside the main search).
+        return FakeLLM(
+            json.dumps(
+                {
+                    "optimized_query": "follow up question",
+                    "start_date": None,
+                    "end_date": None,
+                    "is_recency_query": False,
+                }
+            )
+        )
+
+    async def test_runtime_context_overrides_closure_and_drains_it(self, monkeypatch):
+        """Turn 1 with mentions in BOTH closure and runtime context: the
+        runtime path wins AND the closure is drained so a future turn
+        cannot replay it.
+        """
+        fetched_ids: list[list[int]] = []
+
+        async def fake_fetch_mentioned_documents(*, document_ids, search_space_id):
+            fetched_ids.append(list(document_ids))
+            return []
+
+        async def fake_search_knowledge_base(**_kwargs):
+            return []
+
+        monkeypatch.setattr(
+            "app.agents.new_chat.middleware.knowledge_search.fetch_mentioned_documents",
+            fake_fetch_mentioned_documents,
+        )
+        monkeypatch.setattr(
+            "app.agents.new_chat.middleware.knowledge_search.search_knowledge_base",
+            fake_search_knowledge_base,
+        )
+
+        middleware = KnowledgeBaseSearchMiddleware(
+            llm=self._planner_llm(),
+            search_space_id=42,
+            mentioned_document_ids=[1, 2, 3],
+        )
+
+        await middleware.abefore_agent(
+            {"messages": [HumanMessage(content="what is in those docs?")]},
+            runtime=self._make_runtime([1, 2, 3]),
+        )
+
+        assert fetched_ids == [[1, 2, 3]], (
+            "runtime.context mentions must be the source of truth on turn 1"
+        )
+        assert middleware.mentioned_document_ids == [], (
+            "closure must be drained the first time the runtime path fires "
+            "so no later turn can replay stale mentions"
+        )
+
+    async def test_empty_runtime_context_does_not_replay_closure_mentions(
+        self, monkeypatch
+    ):
+        """Regression: turn 2 with NO mentions must not surface turn 1's
+        mentions from the constructor closure.
+
+        Before the fix, ``if ctx_mentions:`` treated an empty list as
+        absent and fell through to ``elif self.mentioned_document_ids:``,
+        replaying turn 1's mentions. This test pins down the corrected
+        behaviour.
+        """
+        fetched_ids: list[list[int]] = []
+
+        async def fake_fetch_mentioned_documents(*, document_ids, search_space_id):
+            fetched_ids.append(list(document_ids))
+            return []
+
+        async def fake_search_knowledge_base(**_kwargs):
+            return []
+
+        monkeypatch.setattr(
+            "app.agents.new_chat.middleware.knowledge_search.fetch_mentioned_documents",
+            fake_fetch_mentioned_documents,
+        )
+        monkeypatch.setattr(
+            "app.agents.new_chat.middleware.knowledge_search.search_knowledge_base",
+            fake_search_knowledge_base,
+        )
+
+        # Simulate a cached middleware instance whose closure was seeded
+        # by a previous turn's cache-miss build (mentions=[1,2,3]).
+        middleware = KnowledgeBaseSearchMiddleware(
+            llm=self._planner_llm(),
+            search_space_id=42,
+            mentioned_document_ids=[1, 2, 3],
+        )
+
+        # Turn 2: streaming task supplies an EMPTY mention list (no
+        # mentions on this follow-up turn).
+        await middleware.abefore_agent(
+            {"messages": [HumanMessage(content="what about the next steps?")]},
+            runtime=self._make_runtime([]),
+        )
+
+        assert fetched_ids == [], (
+            "fetch_mentioned_documents must NOT be called when the runtime "
+            "context says there are no mentions for this turn"
+        )
+
+    async def test_legacy_path_fires_only_when_runtime_context_absent(
+        self, monkeypatch
+    ):
+        """Backward-compat: if a caller doesn't supply runtime.context (old
+        non-streaming code path), the closure-injected mentions are still
+        honoured exactly once and then drained.
+        """
+        fetched_ids: list[list[int]] = []
+
+        async def fake_fetch_mentioned_documents(*, document_ids, search_space_id):
+            fetched_ids.append(list(document_ids))
+            return []
+
+        async def fake_search_knowledge_base(**_kwargs):
+            return []
+
+        monkeypatch.setattr(
+            "app.agents.new_chat.middleware.knowledge_search.fetch_mentioned_documents",
+            fake_fetch_mentioned_documents,
+        )
+        monkeypatch.setattr(
+            "app.agents.new_chat.middleware.knowledge_search.search_knowledge_base",
+            fake_search_knowledge_base,
+        )
+
+        middleware = KnowledgeBaseSearchMiddleware(
+            llm=self._planner_llm(),
+            search_space_id=42,
+            mentioned_document_ids=[7, 8],
+        )
+
+        # First call: no runtime → legacy path uses the closure.
+        await middleware.abefore_agent(
+            {"messages": [HumanMessage(content="initial question")]},
+            runtime=None,
+        )
+        # Second call: still no runtime — closure already drained, so no replay.
+        await middleware.abefore_agent(
+            {"messages": [HumanMessage(content="follow up")]},
+            runtime=None,
+        )
+
+        assert fetched_ids == [[7, 8]], (
+            "legacy path must honour the closure exactly once and then drain it"
+        )
+        assert middleware.mentioned_document_ids == []

surfsense_backend/tests/unit/test_stream_new_chat_contract.py

@@ -271,6 +271,66 @@ async def test_preflight_skipped_for_auto_router_model():
     await _preflight_llm(fake_llm)
 
 
+@pytest.mark.asyncio
+async def test_settle_speculative_agent_build_swallows_exceptions():
+    """``_settle_speculative_agent_build`` MUST always return cleanly so the
+    caller can safely re-touch the request-scoped session afterwards.
+
+    The helper guards the parallel preflight + agent-build path: when the
+    speculative build is being discarded (429 or non-429 preflight failure)
+    we await it solely to release any in-flight ``AsyncSession`` usage —
+    the build's outcome is irrelevant. Any exception (including
+    ``CancelledError``) leaking out would skip the caller's recovery flow
+    and re-introduce the very session-concurrency hazard the helper exists
+    to prevent.
+    """
+    import asyncio
+
+    from app.tasks.chat.stream_new_chat import _settle_speculative_agent_build
+
+    async def _raises() -> None:
+        raise RuntimeError("speculative build crashed")
+
+    async def _succeeds() -> str:
+        return "agent"
+
+    async def _slow() -> None:
+        await asyncio.sleep(0.05)
+
+    for coro in (_raises(), _succeeds(), _slow()):
+        task = asyncio.create_task(coro)
+        await _settle_speculative_agent_build(task)
+        assert task.done()
+
+
+@pytest.mark.asyncio
+async def test_settle_speculative_agent_build_handles_already_done_task():
+    """Done tasks (success or failure) must still be settled without raising."""
+    import asyncio
+
+    from app.tasks.chat.stream_new_chat import _settle_speculative_agent_build
+
+    async def _ok() -> str:
+        return "ok"
+
+    async def _bad() -> None:
+        raise ValueError("nope")
+
+    ok_task = asyncio.create_task(_ok())
+    bad_task = asyncio.create_task(_bad())
+    # Drive both to completion before settling.
+    await asyncio.sleep(0)
+    await asyncio.sleep(0)
+
+    await _settle_speculative_agent_build(ok_task)
+    await _settle_speculative_agent_build(bad_task)
+    assert ok_task.result() == "ok"
+    # ``bad_task`` exception was consumed by the settle helper; calling
+    # ``.exception()`` after the fact must still return the original error
+    # (the helper observes it but doesn't clear it).
+    assert isinstance(bad_task.exception(), ValueError)
+
+
 def test_stream_exception_classifies_thread_busy():
     exc = BusyError(request_id="thread-123")
     kind, code, severity, is_expected, user_message, extra = _classify_stream_exception(

surfsense_web/components/pricing/pricing-section.tsx

@@ -254,8 +254,8 @@ function PricingFAQ() {
 					Frequently Asked Questions
 				</h2>
 				<p className="mx-auto mt-4 max-w-2xl text-lg text-muted-foreground">
-					Everything you need to know about SurfSense pages, premium credits, and billing. Can&apos;t
-					find what you need? Reach out at{" "}
+					Everything you need to know about SurfSense pages, premium credits, and billing.
+					Can&apos;t find what you need? Reach out at{" "}
 					<a href="mailto:rohan@surfsense.com" className="text-blue-500 underline">
 						rohan@surfsense.com
 					</a>