Merge upstream/dev into feature/multi-agent

surfsense_backend/app/agents/multi_agent_chat/main_agent/graph/compile_graph_sync.py

@@ -11,7 +11,6 @@ from langchain_core.language_models import BaseChatModel
 from langchain_core.tools import BaseTool
 from langgraph.types import Checkpointer
 
-from .middleware import build_main_agent_deepagent_middleware
 from app.agents.multi_agent_chat.subagents.shared.permissions import (
     ToolsPermissions,
 )
@@ -20,6 +19,8 @@ from app.agents.new_chat.feature_flags import AgentFeatureFlags
 from app.agents.new_chat.filesystem_selection import FilesystemMode
 from app.db import ChatVisibility
 
+from .middleware import build_main_agent_deepagent_middleware
+
 
 def build_compiled_agent_graph_sync(
     *,

surfsense_backend/app/agents/multi_agent_chat/main_agent/graph/middleware/checkpointed_subagent_middleware/task_tool.py

@@ -31,8 +31,8 @@ from .propagation import (
 from .resume import (
     build_resume_command,
     fan_out_decisions_to_match,
-    hitlrequest_action_count,
     get_first_pending_subagent_interrupt,
+    hitlrequest_action_count,
 )
 
 logger = logging.getLogger(__name__)
@@ -51,7 +51,9 @@ def build_task_tool_with_parent_config(
     )
 
     if task_description is None:
-        description = TASK_TOOL_DESCRIPTION.format(available_agents=subagent_description_str)
+        description = TASK_TOOL_DESCRIPTION.format(
+            available_agents=subagent_description_str
+        )
     elif "{available_agents}" in task_description:
         description = task_description.format(available_agents=subagent_description_str)
     else:
@@ -90,11 +92,11 @@ def build_task_tool_with_parent_config(
     def task(
         description: Annotated[
             str,
-            "A detailed description of the task for the subagent to perform autonomously. Include all necessary context and specify the expected output format.",  # noqa: E501
+            "A detailed description of the task for the subagent to perform autonomously. Include all necessary context and specify the expected output format.",
         ],
         subagent_type: Annotated[
             str,
-            "The type of subagent to use. Must be one of the available agent types listed in the tool description.",  # noqa: E501
+            "The type of subagent to use. Must be one of the available agent types listed in the tool description.",
         ],
         runtime: ToolRuntime,
     ) -> str | Command:
@@ -119,7 +121,9 @@ def build_task_tool_with_parent_config(
         if callable(get_state):
             try:
                 snapshot = get_state(sub_config)
-                pending_id, pending_value = get_first_pending_subagent_interrupt(snapshot)
+                pending_id, pending_value = get_first_pending_subagent_interrupt(
+                    snapshot
+                )
             except Exception:
                 # Fail loud if a resume is queued: silent fallback would
                 # replay the original interrupt to the user.
@@ -158,11 +162,11 @@ def build_task_tool_with_parent_config(
     async def atask(
         description: Annotated[
             str,
-            "A detailed description of the task for the subagent to perform autonomously. Include all necessary context and specify the expected output format.",  # noqa: E501
+            "A detailed description of the task for the subagent to perform autonomously. Include all necessary context and specify the expected output format.",
         ],
         subagent_type: Annotated[
             str,
-            "The type of subagent to use. Must be one of the available agent types listed in the tool description.",  # noqa: E501
+            "The type of subagent to use. Must be one of the available agent types listed in the tool description.",
         ],
         runtime: ToolRuntime,
     ) -> str | Command:
@@ -186,7 +190,9 @@ def build_task_tool_with_parent_config(
         if callable(aget_state):
             try:
                 snapshot = await aget_state(sub_config)
-                pending_id, pending_value = get_first_pending_subagent_interrupt(snapshot)
+                pending_id, pending_value = get_first_pending_subagent_interrupt(
+                    snapshot
+                )
             except Exception:
                 if has_surfsense_resume(runtime):
                     logger.exception(

surfsense_backend/app/agents/multi_agent_chat/main_agent/graph/middleware/deepagent_stack.py

@@ -23,7 +23,6 @@ from langchain_core.language_models import BaseChatModel
 from langchain_core.tools import BaseTool
 from langgraph.types import Checkpointer
 
-from ...context_prune.prune_tool_names import safe_exclude_tools
 from app.agents.multi_agent_chat.subagents import (
     build_subagents,
     get_subagents_to_exclude,
@@ -66,6 +65,7 @@ from app.agents.new_chat.plugin_loader import (
 from app.agents.new_chat.tools.registry import BUILTIN_TOOLS
 from app.db import ChatVisibility
 
+from ...context_prune.prune_tool_names import safe_exclude_tools
 from .checkpointed_subagent_middleware import SurfSenseCheckpointedSubAgentMiddleware
 
 

surfsense_backend/app/agents/multi_agent_chat/main_agent/runtime/factory.py

@@ -14,8 +14,10 @@ from langchain_core.tools import BaseTool
 from langgraph.types import Checkpointer
 from sqlalchemy.ext.asyncio import AsyncSession
 
-from ..graph.compile_graph_sync import build_compiled_agent_graph_sync
-from ..tools import MAIN_AGENT_SURFSENSE_TOOL_NAMES, MAIN_AGENT_SURFSENSE_TOOL_NAMES_ORDERED
+from app.agents.multi_agent_chat.subagents import (
+    get_subagents_to_exclude,
+    main_prompt_registry_subagent_lines,
+)
 from app.agents.multi_agent_chat.subagents.mcp_tools.index import (
     load_mcp_tools_by_connector,
 )
@@ -24,17 +26,19 @@ from app.agents.new_chat.feature_flags import AgentFeatureFlags, get_flags
 from app.agents.new_chat.filesystem_backends import build_backend_resolver
 from app.agents.new_chat.filesystem_selection import FilesystemMode, FilesystemSelection
 from app.agents.new_chat.llm_config import AgentConfig
-from app.agents.multi_agent_chat.subagents import (
-    get_subagents_to_exclude,
-    main_prompt_registry_subagent_lines,
-)
-from ..system_prompt import build_main_agent_system_prompt
 from app.agents.new_chat.tools.invalid_tool import INVALID_TOOL_NAME, invalid_tool
 from app.agents.new_chat.tools.registry import build_tools_async
 from app.db import ChatVisibility
 from app.services.connector_service import ConnectorService
 from app.utils.perf import get_perf_logger
 
+from ..graph.compile_graph_sync import build_compiled_agent_graph_sync
+from ..system_prompt import build_main_agent_system_prompt
+from ..tools import (
+    MAIN_AGENT_SURFSENSE_TOOL_NAMES,
+    MAIN_AGENT_SURFSENSE_TOOL_NAMES_ORDERED,
+)
+
 _perf_log = get_perf_logger()
 
 

surfsense_backend/app/agents/multi_agent_chat/main_agent/tools/__init__.py

@@ -2,6 +2,9 @@
 
 from __future__ import annotations
 
-from .index import MAIN_AGENT_SURFSENSE_TOOL_NAMES, MAIN_AGENT_SURFSENSE_TOOL_NAMES_ORDERED
+from .index import (
+    MAIN_AGENT_SURFSENSE_TOOL_NAMES,
+    MAIN_AGENT_SURFSENSE_TOOL_NAMES_ORDERED,
+)
 
 __all__ = ["MAIN_AGENT_SURFSENSE_TOOL_NAMES", "MAIN_AGENT_SURFSENSE_TOOL_NAMES_ORDERED"]

surfsense_backend/app/agents/multi_agent_chat/subagents/builtins/deliverables/tools/index.py

@@ -13,7 +13,9 @@ from .resume import create_generate_resume_tool
 from .video_presentation import create_generate_video_presentation_tool
 
 
-def load_tools(*, dependencies: dict[str, Any] | None = None, **kwargs: Any) -> ToolsPermissions:
+def load_tools(
+    *, dependencies: dict[str, Any] | None = None, **kwargs: Any
+) -> ToolsPermissions:
     resolved_dependencies = {**(dependencies or {}), **kwargs}
     podcast = create_generate_podcast_tool(
         search_space_id=resolved_dependencies["search_space_id"],

surfsense_backend/app/agents/multi_agent_chat/subagents/builtins/memory/tools/index.py

@@ -10,7 +10,9 @@ from app.db import ChatVisibility
 from .update_memory import create_update_memory_tool, create_update_team_memory_tool
 
 
-def load_tools(*, dependencies: dict[str, Any] | None = None, **kwargs: Any) -> ToolsPermissions:
+def load_tools(
+    *, dependencies: dict[str, Any] | None = None, **kwargs: Any
+) -> ToolsPermissions:
     resolved_dependencies = {**(dependencies or {}), **kwargs}
     if resolved_dependencies.get("thread_visibility") == ChatVisibility.SEARCH_SPACE:
         mem = create_update_team_memory_tool(
@@ -18,7 +20,10 @@ def load_tools(*, dependencies: dict[str, Any] | None = None, **kwargs: Any) ->
             db_session=resolved_dependencies["db_session"],
             llm=resolved_dependencies.get("llm"),
         )
-        return {"allow": [{"name": getattr(mem, "name", "") or "", "tool": mem}], "ask": []}
+        return {
+            "allow": [{"name": getattr(mem, "name", "") or "", "tool": mem}],
+            "ask": [],
+        }
     mem = create_update_memory_tool(
         user_id=resolved_dependencies["user_id"],
         db_session=resolved_dependencies["db_session"],

surfsense_backend/app/agents/multi_agent_chat/subagents/builtins/research/tools/index.py

@@ -11,14 +11,20 @@ from .search_surfsense_docs import create_search_surfsense_docs_tool
 from .web_search import create_web_search_tool
 
 
-def load_tools(*, dependencies: dict[str, Any] | None = None, **kwargs: Any) -> ToolsPermissions:
+def load_tools(
+    *, dependencies: dict[str, Any] | None = None, **kwargs: Any
+) -> ToolsPermissions:
     resolved_dependencies = {**(dependencies or {}), **kwargs}
     web = create_web_search_tool(
         search_space_id=resolved_dependencies.get("search_space_id"),
         available_connectors=resolved_dependencies.get("available_connectors"),
     )
-    scrape = create_scrape_webpage_tool(firecrawl_api_key=resolved_dependencies.get("firecrawl_api_key"))
-    docs = create_search_surfsense_docs_tool(db_session=resolved_dependencies["db_session"])
+    scrape = create_scrape_webpage_tool(
+        firecrawl_api_key=resolved_dependencies.get("firecrawl_api_key")
+    )
+    docs = create_search_surfsense_docs_tool(
+        db_session=resolved_dependencies["db_session"]
+    )
     return {
         "allow": [
             {"name": getattr(web, "name", "") or "", "tool": web},

surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/airtable/tools/index.py

@@ -7,6 +7,8 @@ from app.agents.multi_agent_chat.subagents.shared.permissions import (
 )
 
 
-def load_tools(*, dependencies: dict[str, Any] | None = None, **kwargs: Any) -> ToolsPermissions:
+def load_tools(
+    *, dependencies: dict[str, Any] | None = None, **kwargs: Any
+) -> ToolsPermissions:
     _ = {**(dependencies or {}), **kwargs}
     return {"allow": [], "ask": []}

surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/calendar/tools/index.py

@@ -12,7 +12,9 @@ from .search_events import create_search_calendar_events_tool
 from .update_event import create_update_calendar_event_tool
 
 
-def load_tools(*, dependencies: dict[str, Any] | None = None, **kwargs: Any) -> ToolsPermissions:
+def load_tools(
+    *, dependencies: dict[str, Any] | None = None, **kwargs: Any
+) -> ToolsPermissions:
     resolved_dependencies = {**(dependencies or {}), **kwargs}
     session_dependencies = {
         "db_session": resolved_dependencies["db_session"],

surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/clickup/tools/index.py

@@ -7,6 +7,8 @@ from app.agents.multi_agent_chat.subagents.shared.permissions import (
 )
 
 
-def load_tools(*, dependencies: dict[str, Any] | None = None, **kwargs: Any) -> ToolsPermissions:
+def load_tools(
+    *, dependencies: dict[str, Any] | None = None, **kwargs: Any
+) -> ToolsPermissions:
     _ = {**(dependencies or {}), **kwargs}
     return {"allow": [], "ask": []}

surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/confluence/tools/index.py

@@ -11,7 +11,9 @@ from .delete_page import create_delete_confluence_page_tool
 from .update_page import create_update_confluence_page_tool
 
 
-def load_tools(*, dependencies: dict[str, Any] | None = None, **kwargs: Any) -> ToolsPermissions:
+def load_tools(
+    *, dependencies: dict[str, Any] | None = None, **kwargs: Any
+) -> ToolsPermissions:
     resolved_dependencies = {**(dependencies or {}), **kwargs}
     session_dependencies = {
         "db_session": resolved_dependencies["db_session"],

surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/discord/tools/index.py

@@ -11,7 +11,9 @@ from .read_messages import create_read_discord_messages_tool
 from .send_message import create_send_discord_message_tool
 
 
-def load_tools(*, dependencies: dict[str, Any] | None = None, **kwargs: Any) -> ToolsPermissions:
+def load_tools(
+    *, dependencies: dict[str, Any] | None = None, **kwargs: Any
+) -> ToolsPermissions:
     d = {**(dependencies or {}), **kwargs}
     common = {
         "db_session": d["db_session"],

surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/dropbox/tools/index.py

@@ -10,7 +10,9 @@ from .create_file import create_create_dropbox_file_tool
 from .trash_file import create_delete_dropbox_file_tool
 
 
-def load_tools(*, dependencies: dict[str, Any] | None = None, **kwargs: Any) -> ToolsPermissions:
+def load_tools(
+    *, dependencies: dict[str, Any] | None = None, **kwargs: Any
+) -> ToolsPermissions:
     d = {**(dependencies or {}), **kwargs}
     common = {
         "db_session": d["db_session"],

surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/gmail/tools/index.py

@@ -14,7 +14,9 @@ from .trash_email import create_trash_gmail_email_tool
 from .update_draft import create_update_gmail_draft_tool
 
 
-def load_tools(*, dependencies: dict[str, Any] | None = None, **kwargs: Any) -> ToolsPermissions:
+def load_tools(
+    *, dependencies: dict[str, Any] | None = None, **kwargs: Any
+) -> ToolsPermissions:
     d = {**(dependencies or {}), **kwargs}
     common = {
         "db_session": d["db_session"],

surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/google_drive/tools/index.py

@@ -10,7 +10,9 @@ from .create_file import create_create_google_drive_file_tool
 from .trash_file import create_delete_google_drive_file_tool
 
 
-def load_tools(*, dependencies: dict[str, Any] | None = None, **kwargs: Any) -> ToolsPermissions:
+def load_tools(
+    *, dependencies: dict[str, Any] | None = None, **kwargs: Any
+) -> ToolsPermissions:
     d = {**(dependencies or {}), **kwargs}
     common = {
         "db_session": d["db_session"],

surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/jira/tools/index.py

@@ -11,7 +11,9 @@ from .delete_issue import create_delete_jira_issue_tool
 from .update_issue import create_update_jira_issue_tool
 
 
-def load_tools(*, dependencies: dict[str, Any] | None = None, **kwargs: Any) -> ToolsPermissions:
+def load_tools(
+    *, dependencies: dict[str, Any] | None = None, **kwargs: Any
+) -> ToolsPermissions:
     d = {**(dependencies or {}), **kwargs}
     common = {
         "db_session": d["db_session"],

surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/linear/tools/index.py

@@ -11,7 +11,9 @@ from .delete_issue import create_delete_linear_issue_tool
 from .update_issue import create_update_linear_issue_tool
 
 
-def load_tools(*, dependencies: dict[str, Any] | None = None, **kwargs: Any) -> ToolsPermissions:
+def load_tools(
+    *, dependencies: dict[str, Any] | None = None, **kwargs: Any
+) -> ToolsPermissions:
     d = {**(dependencies or {}), **kwargs}
     common = {
         "db_session": d["db_session"],

surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/luma/tools/index.py

@@ -11,7 +11,9 @@ from .list_events import create_list_luma_events_tool
 from .read_event import create_read_luma_event_tool
 
 
-def load_tools(*, dependencies: dict[str, Any] | None = None, **kwargs: Any) -> ToolsPermissions:
+def load_tools(
+    *, dependencies: dict[str, Any] | None = None, **kwargs: Any
+) -> ToolsPermissions:
     d = {**(dependencies or {}), **kwargs}
     common = {
         "db_session": d["db_session"],

surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/notion/tools/index.py

@@ -11,7 +11,9 @@ from .delete_page import create_delete_notion_page_tool
 from .update_page import create_update_notion_page_tool
 
 
-def load_tools(*, dependencies: dict[str, Any] | None = None, **kwargs: Any) -> ToolsPermissions:
+def load_tools(
+    *, dependencies: dict[str, Any] | None = None, **kwargs: Any
+) -> ToolsPermissions:
     d = {**(dependencies or {}), **kwargs}
     common = {
         "db_session": d["db_session"],

surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/onedrive/tools/index.py

@@ -10,7 +10,9 @@ from .create_file import create_create_onedrive_file_tool
 from .trash_file import create_delete_onedrive_file_tool
 
 
-def load_tools(*, dependencies: dict[str, Any] | None = None, **kwargs: Any) -> ToolsPermissions:
+def load_tools(
+    *, dependencies: dict[str, Any] | None = None, **kwargs: Any
+) -> ToolsPermissions:
     d = {**(dependencies or {}), **kwargs}
     common = {
         "db_session": d["db_session"],

surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/slack/tools/index.py

@@ -7,6 +7,8 @@ from app.agents.multi_agent_chat.subagents.shared.permissions import (
 )
 
 
-def load_tools(*, dependencies: dict[str, Any] | None = None, **kwargs: Any) -> ToolsPermissions:
+def load_tools(
+    *, dependencies: dict[str, Any] | None = None, **kwargs: Any
+) -> ToolsPermissions:
     _ = {**(dependencies or {}), **kwargs}
     return {"allow": [], "ask": []}

surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/teams/tools/index.py

@@ -11,7 +11,9 @@ from .read_messages import create_read_teams_messages_tool
 from .send_message import create_send_teams_message_tool
 
 
-def load_tools(*, dependencies: dict[str, Any] | None = None, **kwargs: Any) -> ToolsPermissions:
+def load_tools(
+    *, dependencies: dict[str, Any] | None = None, **kwargs: Any
+) -> ToolsPermissions:
     d = {**(dependencies or {}), **kwargs}
     common = {
         "db_session": d["db_session"],

surfsense_backend/app/agents/multi_agent_chat/subagents/mcp_tools/index.py

@@ -31,6 +31,7 @@ logger = logging.getLogger(__name__)
 
 ## Helper functions for fetching connector metadata maps
 
+
 async def fetch_mcp_connector_metadata_maps(
     session: AsyncSession,
     search_space_id: int,
@@ -58,6 +59,7 @@ async def fetch_mcp_connector_metadata_maps(
 
 ## Helper functions for partitioning tools by connector agent
 
+
 def partition_mcp_tools_by_connector(
     tools: Sequence[BaseTool],
     connector_id_to_type: dict[int, str],
@@ -104,8 +106,10 @@ def partition_mcp_tools_by_connector(
 
     return dict(buckets)
 
+
 ## Helper functions for splitting tools by permissions
 
+
 def _get_mcp_tool_name(tool: BaseTool) -> str:
     meta: dict[str, Any] = getattr(tool, "metadata", None) or {}
     orig = meta.get("mcp_original_tool_name")
@@ -139,6 +143,7 @@ def _split_tools_by_permissions(
 
 ## Main function to load MCP tools and split them by permissions for each connector agent
 
+
 async def load_mcp_tools_by_connector(
     session: AsyncSession,
     search_space_id: int,
@@ -148,9 +153,7 @@ async def load_mcp_tools_by_connector(
     Pass ``bypass_internal_hitl=True`` so the subagent's
     ``HumanInTheLoopMiddleware`` is the single HITL gate.
     """
-    flat = await load_mcp_tools(
-        session, search_space_id, bypass_internal_hitl=True
-    )
+    flat = await load_mcp_tools(session, search_space_id, bypass_internal_hitl=True)
     id_map, name_map = await fetch_mcp_connector_metadata_maps(session, search_space_id)
     buckets = partition_mcp_tools_by_connector(flat, id_map, name_map)
     return {

surfsense_backend/app/agents/multi_agent_chat/subagents/registry.py

@@ -8,6 +8,9 @@ from typing import Any, Protocol
 from deepagents import SubAgent
 from langchain_core.language_models import BaseChatModel
 
+from app.agents.multi_agent_chat.constants import (
+    SUBAGENT_TO_REQUIRED_CONNECTOR_MAP,
+)
 from app.agents.multi_agent_chat.subagents.builtins.deliverables.agent import (
     build_subagent as build_deliverables_subagent,
 )
@@ -62,9 +65,6 @@ from app.agents.multi_agent_chat.subagents.connectors.slack.agent import (
 from app.agents.multi_agent_chat.subagents.connectors.teams.agent import (
     build_subagent as build_teams_subagent,
 )
-from app.agents.multi_agent_chat.constants import (
-    SUBAGENT_TO_REQUIRED_CONNECTOR_MAP,
-)
 from app.agents.multi_agent_chat.subagents.shared.md_file_reader import (
     read_md_file,
 )
@@ -105,6 +105,7 @@ SUBAGENT_BUILDERS_BY_NAME: dict[str, SubagentBuilder] = {
     "teams": build_teams_subagent,
 }
 
+
 def _route_resource_package(builder: SubagentBuilder) -> str:
     mod = builder.__module__
     return mod[: -len(".agent")] if mod.endswith(".agent") else mod.rsplit(".", 1)[0]

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

@@ -10,7 +10,9 @@ We use ``create_agent`` (from langchain) rather than ``create_deep_agent``
 This lets us swap in ``SurfSenseFilesystemMiddleware`` — a customisable
 subclass of the default ``FilesystemMiddleware`` — while preserving every
 other behaviour that ``create_deep_agent`` provides (todo-list, subagents,
-summarisation, prompt-caching, etc.).
+summarisation, etc.). Prompt caching is configured at LLM-build time via
+``apply_litellm_prompt_caching`` (LiteLLM-native, multi-provider) rather
+than as a middleware.
 """
 
 import asyncio
@@ -33,12 +35,18 @@ from langchain.agents.middleware import (
     TodoListMiddleware,
     ToolCallLimitMiddleware,
 )
-from langchain_anthropic.middleware import AnthropicPromptCachingMiddleware
 from langchain_core.language_models import BaseChatModel
 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
@@ -52,6 +60,7 @@ from app.agents.new_chat.middleware import (
     DedupHITLToolCallsMiddleware,
     DoomLoopMiddleware,
     FileIntentMiddleware,
+    FlattenSystemMessageMiddleware,
     KnowledgeBasePersistenceMiddleware,
     KnowledgePriorityMiddleware,
     KnowledgeTreeMiddleware,
@@ -74,6 +83,7 @@ from app.agents.new_chat.plugin_loader import (
     load_allowed_plugin_names_from_env,
     load_plugin_middlewares,
 )
+from app.agents.new_chat.prompt_caching import apply_litellm_prompt_caching
 from app.agents.new_chat.subagents import build_specialized_subagents
 from app.agents.new_chat.system_prompt import (
     build_configurable_system_prompt,
@@ -94,6 +104,39 @@ from app.utils.perf import get_perf_logger
 
 _perf_log = get_perf_logger()
 
+
+def _resolve_prompt_model_name(
+    agent_config: AgentConfig | None,
+    llm: BaseChatModel,
+) -> str | None:
+    """Resolve the model id to feed to provider-variant detection.
+
+    Preference order (matches the established idiom in
+    ``llm_router_service.py`` — see ``params.get("base_model") or
+    params.get("model", "")`` usages there):
+
+    1. ``agent_config.litellm_params["base_model"]`` — required for Azure
+       deployments where ``model_name`` is the deployment slug, not the
+       underlying family. Without this, a deployment named e.g.
+       ``"prod-chat-001"`` would silently miss every provider regex.
+    2. ``agent_config.model_name`` — the user's configured model id.
+    3. ``getattr(llm, "model", None)`` — fallback for direct callers that
+       don't supply an ``AgentConfig`` (currently a defensive path; all
+       production callers pass ``agent_config``).
+
+    Returns ``None`` when nothing is available; ``compose_system_prompt``
+    treats that as the ``"default"`` variant (no provider block emitted).
+    """
+    if agent_config is not None:
+        params = agent_config.litellm_params or {}
+        base_model = params.get("base_model")
+        if isinstance(base_model, str) and base_model.strip():
+            return base_model
+        if agent_config.model_name:
+            return agent_config.model_name
+    return getattr(llm, "model", None)
+
+
 # =============================================================================
 # Connector Type Mapping
 # =============================================================================
@@ -279,6 +322,14 @@ async def create_surfsense_deep_agent(
         )
     """
     _t_agent_total = time.perf_counter()
+
+    # Layer thread-aware prompt caching onto the LLM. Idempotent with the
+    # build-time call in ``llm_config.py``; this run merely adds
+    # ``prompt_cache_key=f"surfsense-thread-{thread_id}"`` for OpenAI-family
+    # configs now that ``thread_id`` is known. No-op when ``thread_id`` is
+    # None or the provider is non-OpenAI-family.
+    apply_litellm_prompt_caching(llm, agent_config=agent_config, thread_id=thread_id)
+
     filesystem_selection = filesystem_selection or FilesystemSelection()
     backend_resolver = build_backend_resolver(
         filesystem_selection,
@@ -287,23 +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",
@@ -398,6 +465,7 @@ async def create_surfsense_deep_agent(
             enabled_tool_names=_enabled_tool_names,
             disabled_tool_names=_user_disabled_tool_names,
             mcp_connector_tools=_mcp_connector_tools,
+            model_name=_resolve_prompt_model_name(agent_config, llm),
         )
     else:
         system_prompt = build_surfsense_system_prompt(
@@ -405,6 +473,7 @@ async def create_surfsense_deep_agent(
             enabled_tool_names=_enabled_tool_names,
             disabled_tool_names=_user_disabled_tool_names,
             mcp_connector_tools=_mcp_connector_tools,
+            model_name=_resolve_prompt_model_name(agent_config, llm),
         )
     _perf_log.info(
         "[create_agent] System prompt built in %.3fs", time.perf_counter() - _t0
@@ -424,29 +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(
@@ -568,7 +685,6 @@ def _build_compiled_agent_blocking(
         ),
         create_surfsense_compaction_middleware(llm, StateBackend),
         PatchToolCallsMiddleware(),
-        AnthropicPromptCachingMiddleware(unsupported_model_behavior="ignore"),
     ]
 
     general_purpose_spec: SubAgent = {  # type: ignore[typeddict-unknown-key]
@@ -998,6 +1114,14 @@ 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,
@@ -1010,12 +1134,12 @@ def _build_compiled_agent_blocking(
         action_log_mw,
         PatchToolCallsMiddleware(),
         DedupHITLToolCallsMiddleware(agent_tools=list(tools)),
-        # Plugin slot — sits just before AnthropicCache so plugin-side
-        # transforms see the final tool result and run before any
-        # caching heuristics. Multiple plugins in declared order; loader
-        # filtered by the admin allowlist already.
+        # Plugin slot — sits at the tail so plugin-side transforms see the
+        # final tool result. Prompt caching is now applied at LLM build time
+        # via ``apply_litellm_prompt_caching`` (see prompt_caching.py), so no
+        # caching middleware is needed here. Multiple plugins run in declared
+        # order; loader filtered by the admin allowlist already.
         *plugin_middlewares,
-        AnthropicPromptCachingMiddleware(unsupported_model_behavior="ignore"),
     ]
     deepagent_middleware = [m for m in deepagent_middleware if m is not None]
 

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

@@ -3,8 +3,10 @@ Feature flags for the SurfSense new_chat agent stack.
 
 These flags gate the newer agent middleware (some ported from OpenCode,
 some sourced from ``langchain.agents.middleware`` / ``deepagents``, some
-SurfSense-native). They follow a "default-OFF for risky things,
-default-ON for safe upgrades, master kill-switch for everything new" model.
+SurfSense-native). Most shipped agent-stack upgrades default ON so Docker
+image updates work even when older installs do not have newly introduced
+environment variables. Risky/experimental integrations stay default OFF,
+and the master kill-switch can still disable everything new.
 
 All new middleware checks its flag at agent build time. If the master
 kill-switch ``SURFSENSE_DISABLE_NEW_AGENT_STACK`` is set, every new
@@ -14,16 +16,19 @@ operators a single switch to revert to pre-port behavior.
 Examples
 --------
 
-Local development (recommended for trying everything except doom-loop / selector):
+Defaults:
 
     SURFSENSE_ENABLE_CONTEXT_EDITING=true
     SURFSENSE_ENABLE_COMPACTION_V2=true
     SURFSENSE_ENABLE_RETRY_AFTER=true
+    SURFSENSE_ENABLE_MODEL_FALLBACK=false
+    SURFSENSE_ENABLE_MODEL_CALL_LIMIT=true
+    SURFSENSE_ENABLE_TOOL_CALL_LIMIT=true
     SURFSENSE_ENABLE_TOOL_CALL_REPAIR=true
-    SURFSENSE_ENABLE_PERMISSION=false   # default off, opt-in per deploy
-    SURFSENSE_ENABLE_DOOM_LOOP=false    # default off until UI ships
-    SURFSENSE_ENABLE_LLM_TOOL_SELECTOR=false
-    SURFSENSE_ENABLE_STREAM_PARITY_V2=false  # structured streaming events
+    SURFSENSE_ENABLE_PERMISSION=true
+    SURFSENSE_ENABLE_DOOM_LOOP=true
+    SURFSENSE_ENABLE_LLM_TOOL_SELECTOR=false  # adds a per-turn LLM call
+    SURFSENSE_ENABLE_STREAM_PARITY_V2=true
 
 Master kill-switch (overrides everything else):
 
@@ -60,32 +65,28 @@ class AgentFeatureFlags:
     disable_new_agent_stack: bool = False
 
     # Agent quality — context budget, retry/limits, name-repair, doom-loop
-    enable_context_editing: bool = False
-    enable_compaction_v2: bool = False
-    enable_retry_after: bool = False
+    enable_context_editing: bool = True
+    enable_compaction_v2: bool = True
+    enable_retry_after: bool = True
     enable_model_fallback: bool = False
-    enable_model_call_limit: bool = False
-    enable_tool_call_limit: bool = False
-    enable_tool_call_repair: bool = False
-    enable_doom_loop: bool = (
-        False  # Default OFF until UI handles permission='doom_loop'
-    )
+    enable_model_call_limit: bool = True
+    enable_tool_call_limit: bool = True
+    enable_tool_call_repair: bool = True
+    enable_doom_loop: bool = True
 
     # Safety — permissions, concurrency, tool-set narrowing
-    enable_permission: bool = False  # Default OFF for first deploy
-    enable_busy_mutex: bool = False
+    enable_permission: bool = True
+    enable_busy_mutex: bool = True
     enable_llm_tool_selector: bool = False  # Default OFF — adds per-turn LLM cost
 
     # Skills + subagents
-    enable_skills: bool = False
-    enable_specialized_subagents: bool = False
-    enable_kb_planner_runnable: bool = False
+    enable_skills: bool = True
+    enable_specialized_subagents: bool = True
+    enable_kb_planner_runnable: bool = True
 
     # Snapshot / revert
-    enable_action_log: bool = False
-    enable_revert_route: bool = (
-        False  # Backend ships before UI; route returns 503 until this flips
-    )
+    enable_action_log: bool = True
+    enable_revert_route: bool = True
 
     # Streaming parity v2 — opt in to LangChain's structured
     # ``AIMessageChunk`` content (typed reasoning blocks, tool-input
@@ -94,7 +95,7 @@ class AgentFeatureFlags:
     # text path and the synthetic ``call_<run_id>`` tool-call id (no
     # ``langchainToolCallId`` propagation). Schema migrations 135/136
     # ship unconditionally because they're forward-compatible.
-    enable_stream_parity_v2: bool = False
+    enable_stream_parity_v2: bool = True
 
     # Plugins
     enable_plugin_loader: bool = False
@@ -102,6 +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.
@@ -115,48 +151,76 @@ class AgentFeatureFlags:
                 "SURFSENSE_DISABLE_NEW_AGENT_STACK is set: every new agent "
                 "middleware is forced OFF for this build."
             )
-            return cls(disable_new_agent_stack=True)
+            return cls(
+                disable_new_agent_stack=True,
+                enable_context_editing=False,
+                enable_compaction_v2=False,
+                enable_retry_after=False,
+                enable_model_fallback=False,
+                enable_model_call_limit=False,
+                enable_tool_call_limit=False,
+                enable_tool_call_repair=False,
+                enable_doom_loop=False,
+                enable_permission=False,
+                enable_busy_mutex=False,
+                enable_llm_tool_selector=False,
+                enable_skills=False,
+                enable_specialized_subagents=False,
+                enable_kb_planner_runnable=False,
+                enable_action_log=False,
+                enable_revert_route=False,
+                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(
             disable_new_agent_stack=False,
             # Agent quality
-            enable_context_editing=_env_bool("SURFSENSE_ENABLE_CONTEXT_EDITING", False),
-            enable_compaction_v2=_env_bool("SURFSENSE_ENABLE_COMPACTION_V2", False),
-            enable_retry_after=_env_bool("SURFSENSE_ENABLE_RETRY_AFTER", False),
+            enable_context_editing=_env_bool("SURFSENSE_ENABLE_CONTEXT_EDITING", True),
+            enable_compaction_v2=_env_bool("SURFSENSE_ENABLE_COMPACTION_V2", True),
+            enable_retry_after=_env_bool("SURFSENSE_ENABLE_RETRY_AFTER", True),
             enable_model_fallback=_env_bool("SURFSENSE_ENABLE_MODEL_FALLBACK", False),
             enable_model_call_limit=_env_bool(
-                "SURFSENSE_ENABLE_MODEL_CALL_LIMIT", False
+                "SURFSENSE_ENABLE_MODEL_CALL_LIMIT", True
             ),
-            enable_tool_call_limit=_env_bool("SURFSENSE_ENABLE_TOOL_CALL_LIMIT", False),
+            enable_tool_call_limit=_env_bool("SURFSENSE_ENABLE_TOOL_CALL_LIMIT", True),
             enable_tool_call_repair=_env_bool(
-                "SURFSENSE_ENABLE_TOOL_CALL_REPAIR", False
+                "SURFSENSE_ENABLE_TOOL_CALL_REPAIR", True
             ),
-            enable_doom_loop=_env_bool("SURFSENSE_ENABLE_DOOM_LOOP", False),
+            enable_doom_loop=_env_bool("SURFSENSE_ENABLE_DOOM_LOOP", True),
             # Safety
-            enable_permission=_env_bool("SURFSENSE_ENABLE_PERMISSION", False),
-            enable_busy_mutex=_env_bool("SURFSENSE_ENABLE_BUSY_MUTEX", False),
+            enable_permission=_env_bool("SURFSENSE_ENABLE_PERMISSION", True),
+            enable_busy_mutex=_env_bool("SURFSENSE_ENABLE_BUSY_MUTEX", True),
             enable_llm_tool_selector=_env_bool(
                 "SURFSENSE_ENABLE_LLM_TOOL_SELECTOR", False
             ),
             # Skills + subagents
-            enable_skills=_env_bool("SURFSENSE_ENABLE_SKILLS", False),
+            enable_skills=_env_bool("SURFSENSE_ENABLE_SKILLS", True),
             enable_specialized_subagents=_env_bool(
-                "SURFSENSE_ENABLE_SPECIALIZED_SUBAGENTS", False
+                "SURFSENSE_ENABLE_SPECIALIZED_SUBAGENTS", True
             ),
             enable_kb_planner_runnable=_env_bool(
-                "SURFSENSE_ENABLE_KB_PLANNER_RUNNABLE", False
+                "SURFSENSE_ENABLE_KB_PLANNER_RUNNABLE", True
             ),
             # Snapshot / revert
-            enable_action_log=_env_bool("SURFSENSE_ENABLE_ACTION_LOG", False),
-            enable_revert_route=_env_bool("SURFSENSE_ENABLE_REVERT_ROUTE", False),
+            enable_action_log=_env_bool("SURFSENSE_ENABLE_ACTION_LOG", True),
+            enable_revert_route=_env_bool("SURFSENSE_ENABLE_REVERT_ROUTE", True),
             # Streaming parity v2
             enable_stream_parity_v2=_env_bool(
-                "SURFSENSE_ENABLE_STREAM_PARITY_V2", False
+                "SURFSENSE_ENABLE_STREAM_PARITY_V2", True
             ),
             # Plugins
             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/llm_config.py

@@ -27,6 +27,7 @@ from litellm import get_model_info
 from sqlalchemy import select
 from sqlalchemy.ext.asyncio import AsyncSession
 
+from app.agents.new_chat.prompt_caching import apply_litellm_prompt_caching
 from app.services.llm_router_service import (
     AUTO_MODE_ID,
     ChatLiteLLMRouter,
@@ -89,41 +90,18 @@ class SanitizedChatLiteLLM(ChatLiteLLM):
             yield chunk
 
 
-# Provider mapping for LiteLLM model string construction
-PROVIDER_MAP = {
-    "OPENAI": "openai",
-    "ANTHROPIC": "anthropic",
-    "GROQ": "groq",
-    "COHERE": "cohere",
-    "GOOGLE": "gemini",
-    "OLLAMA": "ollama_chat",
-    "MISTRAL": "mistral",
-    "AZURE_OPENAI": "azure",
-    "OPENROUTER": "openrouter",
-    "XAI": "xai",
-    "BEDROCK": "bedrock",
-    "VERTEX_AI": "vertex_ai",
-    "TOGETHER_AI": "together_ai",
-    "FIREWORKS_AI": "fireworks_ai",
-    "DEEPSEEK": "openai",
-    "ALIBABA_QWEN": "openai",
-    "MOONSHOT": "openai",
-    "ZHIPU": "openai",
-    "GITHUB_MODELS": "github",
-    "REPLICATE": "replicate",
-    "PERPLEXITY": "perplexity",
-    "ANYSCALE": "anyscale",
-    "DEEPINFRA": "deepinfra",
-    "CEREBRAS": "cerebras",
-    "SAMBANOVA": "sambanova",
-    "AI21": "ai21",
-    "CLOUDFLARE": "cloudflare",
-    "DATABRICKS": "databricks",
-    "COMETAPI": "cometapi",
-    "HUGGINGFACE": "huggingface",
-    "MINIMAX": "openai",
-    "CUSTOM": "custom",
-}
+# Provider mapping for LiteLLM model string construction.
+#
+# Single source of truth lives in
+# :mod:`app.services.provider_capabilities` so the YAML loader (which
+# runs during ``app.config`` class-body init) can resolve provider
+# prefixes without dragging the agent / tools tree into module load
+# order. Re-exported here under the historical ``PROVIDER_MAP`` name
+# so existing callers (``llm_router_service``, ``image_gen_router_service``,
+# tests) keep working unchanged.
+from app.services.provider_capabilities import (  # noqa: E402
+    _PROVIDER_PREFIX_MAP as PROVIDER_MAP,
+)
 
 
 def _attach_model_profile(llm: ChatLiteLLM, model_string: str) -> None:
@@ -177,6 +155,17 @@ class AgentConfig:
     anonymous_enabled: bool = False
     quota_reserve_tokens: int | None = None
 
+    # Capability flag: best-effort True for the chat selector / catalog.
+    # Resolved via :func:`provider_capabilities.derive_supports_image_input`
+    # which prefers OpenRouter's ``architecture.input_modalities`` and
+    # otherwise consults LiteLLM's authoritative model map. Default True
+    # is the conservative-allow stance — the streaming-task safety net
+    # (``is_known_text_only_chat_model``) is the *only* place a False
+    # actually blocks a request. Setting this to False here without an
+    # authoritative source would silently hide vision-capable models
+    # (the regression we're fixing).
+    supports_image_input: bool = True
+
     @classmethod
     def from_auto_mode(cls) -> "AgentConfig":
         """
@@ -202,6 +191,12 @@ class AgentConfig:
             is_premium=False,
             anonymous_enabled=False,
             quota_reserve_tokens=None,
+            # Auto routes across the configured pool, which usually
+            # contains at least one vision-capable deployment; the router
+            # will surface a 404 from a non-vision deployment as a normal
+            # ``allowed_fails`` event and fail over rather than blocking
+            # the request outright.
+            supports_image_input=True,
         )
 
     @classmethod
@@ -215,10 +210,24 @@ class AgentConfig:
         Returns:
             AgentConfig instance
         """
-        return cls(
-            provider=config.provider.value
+        # Lazy import to avoid pulling provider_capabilities (and its
+        # transitive litellm import) into module-init order.
+        from app.services.provider_capabilities import derive_supports_image_input
+
+        provider_value = (
+            config.provider.value
             if hasattr(config.provider, "value")
-            else str(config.provider),
+            else str(config.provider)
+        )
+        litellm_params = config.litellm_params or {}
+        base_model = (
+            litellm_params.get("base_model")
+            if isinstance(litellm_params, dict)
+            else None
+        )
+
+        return cls(
+            provider=provider_value,
             model_name=config.model_name,
             api_key=config.api_key,
             api_base=config.api_base,
@@ -234,6 +243,16 @@ class AgentConfig:
             is_premium=False,
             anonymous_enabled=False,
             quota_reserve_tokens=None,
+            # BYOK rows have no operator-curated capability flag, so we
+            # ask LiteLLM (default-allow on unknown). The streaming
+            # safety net still blocks if the model is *explicitly*
+            # marked text-only.
+            supports_image_input=derive_supports_image_input(
+                provider=provider_value,
+                model_name=config.model_name,
+                base_model=base_model,
+                custom_provider=config.custom_provider,
+            ),
         )
 
     @classmethod
@@ -252,15 +271,46 @@ class AgentConfig:
         Returns:
             AgentConfig instance
         """
+        # Lazy import to avoid pulling provider_capabilities (and its
+        # transitive litellm import) into module-init order.
+        from app.services.provider_capabilities import derive_supports_image_input
+
         # Get system instructions from YAML, default to empty string
         system_instructions = yaml_config.get("system_instructions", "")
 
+        provider = yaml_config.get("provider", "").upper()
+        model_name = yaml_config.get("model_name", "")
+        custom_provider = yaml_config.get("custom_provider")
+        litellm_params = yaml_config.get("litellm_params") or {}
+        base_model = (
+            litellm_params.get("base_model")
+            if isinstance(litellm_params, dict)
+            else None
+        )
+
+        # Explicit YAML override wins; otherwise derive from LiteLLM /
+        # OpenRouter modalities. The YAML loader already populates this
+        # field, but this method is also called from
+        # ``load_global_llm_config_by_id``'s file fallback (hot reload),
+        # so we re-derive here for safety. The bool() coercion preserves
+        # the loader's behaviour for explicit ``true`` / ``false``
+        # strings that PyYAML may surface.
+        if "supports_image_input" in yaml_config:
+            supports_image_input = bool(yaml_config.get("supports_image_input"))
+        else:
+            supports_image_input = derive_supports_image_input(
+                provider=provider,
+                model_name=model_name,
+                base_model=base_model,
+                custom_provider=custom_provider,
+            )
+
         return cls(
-            provider=yaml_config.get("provider", "").upper(),
-            model_name=yaml_config.get("model_name", ""),
+            provider=provider,
+            model_name=model_name,
             api_key=yaml_config.get("api_key", ""),
             api_base=yaml_config.get("api_base"),
-            custom_provider=yaml_config.get("custom_provider"),
+            custom_provider=custom_provider,
             litellm_params=yaml_config.get("litellm_params"),
             # Prompt configuration from YAML (with defaults for backwards compatibility)
             system_instructions=system_instructions if system_instructions else None,
@@ -275,6 +325,7 @@ class AgentConfig:
             is_premium=yaml_config.get("billing_tier", "free") == "premium",
             anonymous_enabled=yaml_config.get("anonymous_enabled", False),
             quota_reserve_tokens=yaml_config.get("quota_reserve_tokens"),
+            supports_image_input=supports_image_input,
         )
 
 
@@ -494,6 +545,11 @@ def create_chat_litellm_from_config(llm_config: dict) -> ChatLiteLLM | None:
 
     llm = SanitizedChatLiteLLM(**litellm_kwargs)
     _attach_model_profile(llm, model_string)
+    # Configure LiteLLM-native prompt caching (cache_control_injection_points
+    # for Anthropic/Bedrock/Vertex/Gemini/Azure-AI/OpenRouter/Databricks/etc.).
+    # ``agent_config=None`` here — the YAML path doesn't have provider intent
+    # in a structured form, so we set only the universal injection points.
+    apply_litellm_prompt_caching(llm)
     return llm
 
 
@@ -518,7 +574,16 @@ def create_chat_litellm_from_agent_config(
             print("Error: Auto mode requested but LLM Router not initialized")
             return None
         try:
-            return get_auto_mode_llm()
+            router_llm = get_auto_mode_llm()
+            if router_llm is not None:
+                # Universal cache_control_injection_points only — auto-mode
+                # fans out across providers, so OpenAI-only kwargs (e.g.
+                # ``prompt_cache_key``) are left off here. ``drop_params``
+                # would strip them at the provider boundary anyway, but
+                # there's no point setting them when we don't know the
+                # destination.
+                apply_litellm_prompt_caching(router_llm, agent_config=agent_config)
+            return router_llm
         except Exception as e:
             print(f"Error creating ChatLiteLLMRouter: {e}")
             return None
@@ -549,4 +614,9 @@ def create_chat_litellm_from_agent_config(
 
     llm = SanitizedChatLiteLLM(**litellm_kwargs)
     _attach_model_profile(llm, model_string)
+    # Build-time prompt caching: sets ``cache_control_injection_points`` for
+    # all providers and (for OpenAI/DeepSeek/xAI) ``prompt_cache_retention``.
+    # Per-thread ``prompt_cache_key`` is layered on later in
+    # ``create_surfsense_deep_agent`` once ``thread_id`` is known.
+    apply_litellm_prompt_caching(llm, agent_config=agent_config)
     return llm

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/busy_mutex.py

@@ -33,6 +33,7 @@ from __future__ import annotations
 
 import asyncio
 import logging
+import time
 import weakref
 from typing import Any
 
@@ -58,6 +59,11 @@ class _ThreadLockManager:
             weakref.WeakValueDictionary()
         )
         self._cancel_events: dict[str, asyncio.Event] = {}
+        self._cancel_requested_at_ms: dict[str, int] = {}
+        self._cancel_attempt_count: dict[str, int] = {}
+        # Monotonic per-thread epoch used to prevent stale middleware
+        # teardown from releasing a newer turn's lock.
+        self._turn_epoch: dict[str, int] = {}
 
     def lock_for(self, thread_id: str) -> asyncio.Lock:
         lock = self._locks.get(thread_id)
@@ -76,14 +82,57 @@ class _ThreadLockManager:
     def request_cancel(self, thread_id: str) -> bool:
         event = self._cancel_events.get(thread_id)
         if event is None:
-            return False
+            event = asyncio.Event()
+            self._cancel_events[thread_id] = event
         event.set()
+        now_ms = int(time.time() * 1000)
+        self._cancel_requested_at_ms[thread_id] = now_ms
+        self._cancel_attempt_count[thread_id] = (
+            self._cancel_attempt_count.get(thread_id, 0) + 1
+        )
         return True
 
+    def is_cancel_requested(self, thread_id: str) -> bool:
+        event = self._cancel_events.get(thread_id)
+        return bool(event and event.is_set())
+
+    def cancel_state(self, thread_id: str) -> tuple[int, int] | None:
+        if not self.is_cancel_requested(thread_id):
+            return None
+        attempts = self._cancel_attempt_count.get(thread_id, 1)
+        requested_at_ms = self._cancel_requested_at_ms.get(thread_id, 0)
+        return attempts, requested_at_ms
+
     def reset(self, thread_id: str) -> None:
         event = self._cancel_events.get(thread_id)
         if event is not None:
             event.clear()
+        self._cancel_requested_at_ms.pop(thread_id, None)
+        self._cancel_attempt_count.pop(thread_id, None)
+
+    def bump_turn_epoch(self, thread_id: str) -> int:
+        epoch = self._turn_epoch.get(thread_id, 0) + 1
+        self._turn_epoch[thread_id] = epoch
+        return epoch
+
+    def current_turn_epoch(self, thread_id: str) -> int:
+        return self._turn_epoch.get(thread_id, 0)
+
+    def end_turn(self, thread_id: str) -> None:
+        """Best-effort terminal cleanup for a thread turn.
+
+        This is intentionally idempotent and safe to call from outer stream
+        finally-blocks where middleware teardown might be skipped due to abort
+        or disconnect edge-cases.
+        """
+        # Invalidate any in-flight middleware holder first. This guarantees a
+        # stale ``aafter_agent`` from an older attempt cannot unlock a newer
+        # retry that already acquired the lock for the same thread.
+        self.bump_turn_epoch(thread_id)
+        lock = self._locks.get(thread_id)
+        if lock is not None and lock.locked():
+            lock.release()
+        self.reset(thread_id)
 
     def release(self, thread_id: str) -> bool:
         """Force-release the per-thread lock; safety-net for turns that end before ``__end__``.
@@ -115,18 +164,28 @@ def get_cancel_event(thread_id: str) -> asyncio.Event:
 
 
 def request_cancel(thread_id: str) -> bool:
-    """Trip the cancel event for ``thread_id``. Returns True if found."""
+    """Trip the cancel event for ``thread_id``. Always returns True."""
     return manager.request_cancel(thread_id)
 
 
+def is_cancel_requested(thread_id: str) -> bool:
+    """Return whether ``thread_id`` currently has a pending cancel signal."""
+    return manager.is_cancel_requested(thread_id)
+
+
+def get_cancel_state(thread_id: str) -> tuple[int, int] | None:
+    """Return ``(attempt_count, requested_at_ms)`` for pending cancel state."""
+    return manager.cancel_state(thread_id)
+
+
 def reset_cancel(thread_id: str) -> None:
     """Reset the cancel event for ``thread_id`` (called between turns)."""
     manager.reset(thread_id)
 
 
-def release_lock(thread_id: str) -> bool:
-    """Force-release the per-thread busy lock; safe to call when not held."""
-    return manager.release(thread_id)
+def end_turn(thread_id: str) -> None:
+    """Force end-of-turn cleanup for lock + cancel state."""
+    manager.end_turn(thread_id)
 
 
 class BusyMutexMiddleware(AgentMiddleware[AgentState[ResponseT], ContextT, ResponseT]):
@@ -151,10 +210,10 @@ class BusyMutexMiddleware(AgentMiddleware[AgentState[ResponseT], ContextT, Respo
         super().__init__()
         self._require_thread_id = require_thread_id
         self.tools = []
-        # Per-call locks owned by this middleware. We track them as
-        # an instance attribute so ``aafter_agent`` knows which lock
-        # to release.
-        self._held_locks: dict[str, asyncio.Lock] = {}
+        # Per-call lock ownership tracked as (lock, epoch). ``aafter_agent``
+        # only releases when its epoch still matches the manager's current
+        # epoch for the thread, preventing stale unlock races.
+        self._held_locks: dict[str, tuple[asyncio.Lock, int]] = {}
 
     @staticmethod
     def _thread_id(runtime: Runtime[ContextT]) -> str | None:
@@ -205,7 +264,8 @@ class BusyMutexMiddleware(AgentMiddleware[AgentState[ResponseT], ContextT, Respo
         if lock.locked():
             raise BusyError(request_id=thread_id)
         await lock.acquire()
-        self._held_locks[thread_id] = lock
+        epoch = manager.bump_turn_epoch(thread_id)
+        self._held_locks[thread_id] = (lock, epoch)
         # Reset the cancel event so this turn starts fresh
         reset_cancel(thread_id)
         return None
@@ -219,8 +279,15 @@ class BusyMutexMiddleware(AgentMiddleware[AgentState[ResponseT], ContextT, Respo
         thread_id = self._thread_id(runtime)
         if thread_id is None:
             return None
-        lock = self._held_locks.pop(thread_id, None)
-        if lock is not None and lock.locked():
+        held = self._held_locks.pop(thread_id, None)
+        if held is None:
+            return None
+        lock, held_epoch = held
+        if held_epoch != manager.current_turn_epoch(thread_id):
+            # Stale teardown from an older attempt (e.g. runtime-recovery path
+            # already advanced epoch). Do not touch current lock/cancel state.
+            return None
+        if lock.locked():
             lock.release()
         # Always clear cancel event between turns so a stale signal
         # doesn't leak into the next request.
@@ -251,9 +318,11 @@ class BusyMutexMiddleware(AgentMiddleware[AgentState[ResponseT], ContextT, Respo
 
 __all__ = [
     "BusyMutexMiddleware",
+    "end_turn",
     "get_cancel_event",
+    "get_cancel_state",
+    "is_cancel_requested",
     "manager",
-    "release_lock",
     "request_cancel",
     "reset_cancel",
 ]

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

@@ -0,0 +1,188 @@
+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)``
+gate always failed) with LiteLLM's universal caching mechanism.
+
+Coverage:
+
+- Marker-based providers (need ``cache_control`` injection, which LiteLLM
+  performs automatically when ``cache_control_injection_points`` is set):
+  ``anthropic/``, ``bedrock/``, ``vertex_ai/``, ``gemini/``, ``azure_ai/``,
+  ``openrouter/`` (Claude/Gemini/MiniMax/GLM/z-ai routes), ``databricks/``
+  (Claude), ``dashscope/`` (Qwen), ``minimax/``, ``zai/`` (GLM).
+- Auto-cached (LiteLLM strips the marker silently): ``openai/``,
+  ``deepseek/``, ``xai/`` — these caches automatically for prompts ≥1024
+  tokens and surface ``prompt_cache_key`` / ``prompt_cache_retention``.
+
+We inject **two** breakpoints per request:
+
+- ``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.
+
+For OpenAI-family configs we additionally pass:
+
+- ``prompt_cache_key=f"surfsense-thread-{thread_id}"`` — routing hint that
+  raises hit rate by sending requests with a shared prefix to the same
+  backend.
+- ``prompt_cache_retention="24h"`` — extends cache TTL beyond the default
+  5-10 min in-memory cache.
+
+Safety net: ``litellm.drop_params=True`` is set globally in
+``app.services.llm_service`` at module-load time. Any kwarg the destination
+provider doesn't recognise is auto-stripped at the provider transformer
+layer, so an OpenAI→Bedrock auto-mode fallback can't 400 on
+``prompt_cache_key`` etc.
+"""
+
+from __future__ import annotations
+
+import logging
+from typing import TYPE_CHECKING, Any
+
+from langchain_core.language_models import BaseChatModel
+
+if TYPE_CHECKING:
+    from app.agents.new_chat.llm_config import AgentConfig
+
+logger = logging.getLogger(__name__)
+
+
+# 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", "index": 0},
+    {"location": "message", "index": -1},
+)
+
+# Providers (uppercase ``AgentConfig.provider`` values) that natively expose
+# OpenAI-style automatic prompt caching with ``prompt_cache_key`` and
+# ``prompt_cache_retention`` kwargs. Strict whitelist — many other providers
+# in ``PROVIDER_MAP`` route through litellm's ``openai`` prefix without
+# implementing the OpenAI prompt-cache surface (e.g. MOONSHOT, ZHIPU,
+# MINIMAX), so we can't infer family from the litellm prefix alone.
+_OPENAI_FAMILY_PROVIDERS: frozenset[str] = frozenset({"OPENAI", "DEEPSEEK", "XAI"})
+
+
+def _is_router_llm(llm: BaseChatModel) -> bool:
+    """Detect ``ChatLiteLLMRouter`` (auto-mode) without an eager import.
+
+    Importing ``app.services.llm_router_service`` at module-load time would
+    create a cycle via ``llm_config -> prompt_caching -> llm_router_service``.
+    Class-name comparison is sufficient since the class is defined in a
+    single place.
+    """
+    return type(llm).__name__ == "ChatLiteLLMRouter"
+
+
+def _is_openai_family_config(agent_config: AgentConfig | None) -> bool:
+    """Whether the config targets an OpenAI-style prompt-cache surface.
+
+    Strict — only returns True when the user explicitly chose OPENAI,
+    DEEPSEEK, or XAI as the provider in their ``NewLLMConfig`` /
+    ``YAMLConfig``. Auto-mode and custom providers return False because
+    we can't statically know the destination.
+    """
+    if agent_config is None or not agent_config.provider:
+        return False
+    if agent_config.is_auto_mode:
+        return False
+    if agent_config.custom_provider:
+        return False
+    return agent_config.provider.upper() in _OPENAI_FAMILY_PROVIDERS
+
+
+def _get_or_init_model_kwargs(llm: BaseChatModel) -> dict[str, Any] | None:
+    """Return ``llm.model_kwargs`` as a writable dict, or ``None`` to bail.
+
+    Initialises the field to ``{}`` when present-but-None on a Pydantic v2
+    model. Returns ``None`` if the LLM type doesn't expose a writable
+    ``model_kwargs`` attribute (caller should treat as no-op).
+    """
+    model_kwargs = getattr(llm, "model_kwargs", None)
+    if isinstance(model_kwargs, dict):
+        return model_kwargs
+    try:
+        llm.model_kwargs = {}  # type: ignore[attr-defined]
+    except Exception:
+        return None
+    refreshed = getattr(llm, "model_kwargs", None)
+    return refreshed if isinstance(refreshed, dict) else None
+
+
+def apply_litellm_prompt_caching(
+    llm: BaseChatModel,
+    *,
+    agent_config: AgentConfig | None = None,
+    thread_id: int | None = None,
+) -> None:
+    """Configure LiteLLM prompt caching on a ChatLiteLLM/ChatLiteLLMRouter.
+
+    Idempotent — values already present in ``llm.model_kwargs`` (e.g. from
+    ``agent_config.litellm_params`` overrides) are preserved. Mutates
+    ``llm.model_kwargs`` in place; the kwargs flow to ``litellm.completion``
+    via ``ChatLiteLLM._default_params`` and via ``self.model_kwargs`` merge
+    in our custom ``ChatLiteLLMRouter``.
+
+    Args:
+        llm: ChatLiteLLM, SanitizedChatLiteLLM, or ChatLiteLLMRouter instance.
+        agent_config: Optional ``AgentConfig`` driving provider-specific
+            behaviour. When omitted (or auto-mode), only the universal
+            ``cache_control_injection_points`` are set.
+        thread_id: Optional thread id used to construct a per-thread
+            ``prompt_cache_key`` for OpenAI-family providers. Caching still
+            works without it (server-side automatic), but the key improves
+            backend routing affinity and therefore hit rate.
+    """
+    model_kwargs = _get_or_init_model_kwargs(llm)
+    if model_kwargs is None:
+        logger.debug(
+            "apply_litellm_prompt_caching: %s exposes no writable model_kwargs; skipping",
+            type(llm).__name__,
+        )
+        return
+
+    if "cache_control_injection_points" not in model_kwargs:
+        model_kwargs["cache_control_injection_points"] = [
+            dict(point) for point in _DEFAULT_INJECTION_POINTS
+        ]
+
+    # OpenAI-family extras only when we statically know the destination is
+    # OpenAI / DeepSeek / xAI. Auto-mode router fans out across providers
+    # so we can't safely set OpenAI-only kwargs there (drop_params would
+    # strip them but it's wasteful to set them in the first place).
+    if _is_router_llm(llm):
+        return
+    if not _is_openai_family_config(agent_config):
+        return
+
+    if thread_id is not None and "prompt_cache_key" not in model_kwargs:
+        model_kwargs["prompt_cache_key"] = f"surfsense-thread-{thread_id}"
+    if "prompt_cache_retention" not in model_kwargs:
+        model_kwargs["prompt_cache_retention"] = "24h"

surfsense_backend/app/agents/new_chat/subagents/constants.py

@@ -27,14 +27,9 @@ WRITE_TOOL_DENY_PATTERNS: tuple[str, ...] = (
 NON_PROVIDER_STATE_MUTATION_DENY: frozenset[str] = frozenset(
     {
         # Exact tool names from shared deny patterns.
-        *{
-            name
-            for name in WRITE_TOOL_DENY_PATTERNS
-            if "*" not in name
-        },
+        *{name for name in WRITE_TOOL_DENY_PATTERNS if "*" not in name},
         # Additional non-provider state mutation controls.
         "write_todos",
         "task",
     }
 )
-

surfsense_backend/app/agents/new_chat/subagents/providers/linear.py

@@ -112,10 +112,7 @@ def _permission_middleware(*, selected_tools: Sequence[BaseTool]) -> Any:
         Rule(permission=name, pattern="*", action="deny")
         for name in NON_PROVIDER_STATE_MUTATION_DENY
     )
-    rules.extend(
-        Rule(permission=name, pattern="*", action="ask")
-        for name in ask_tools
-    )
+    rules.extend(Rule(permission=name, pattern="*", action="ask") for name in ask_tools)
     return PermissionMiddleware(
         rulesets=[Ruleset(rules=rules, origin="subagent_linear_specialist")]
     )
@@ -163,4 +160,3 @@ def build_linear_specialist_subagent(
     if model is not None:
         spec["model"] = model
     return spec  # type: ignore[return-value]
-

surfsense_backend/app/agents/new_chat/subagents/providers/slack.py

@@ -119,10 +119,7 @@ def _permission_middleware(*, selected_tools: Sequence[BaseTool]) -> Any:
         Rule(permission=name, pattern="*", action="deny")
         for name in NON_PROVIDER_STATE_MUTATION_DENY
     )
-    rules.extend(
-        Rule(permission=name, pattern="*", action="ask")
-        for name in ask_tools
-    )
+    rules.extend(Rule(permission=name, pattern="*", action="ask") for name in ask_tools)
     return PermissionMiddleware(
         rulesets=[Ruleset(rules=rules, origin="subagent_slack_specialist")]
     )
@@ -171,4 +168,3 @@ def build_slack_specialist_subagent(
     if model is not None:
         spec["model"] = model
     return spec  # type: ignore[return-value]
-

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/generate_image.py

@@ -31,6 +31,7 @@ from app.services.image_gen_router_service import (
     ImageGenRouterService,
     is_image_gen_auto_mode,
 )
+from app.services.provider_api_base import resolve_api_base
 from app.utils.signed_image_urls import generate_image_token
 
 logger = logging.getLogger(__name__)
@@ -49,12 +50,16 @@ _PROVIDER_MAP = {
 }
 
 
+def _resolve_provider_prefix(provider: str, custom_provider: str | None) -> str:
+    if custom_provider:
+        return custom_provider
+    return _PROVIDER_MAP.get(provider.upper(), provider.lower())
+
+
 def _build_model_string(
     provider: str, model_name: str, custom_provider: str | None
 ) -> str:
-    if custom_provider:
-        return f"{custom_provider}/{model_name}"
-    prefix = _PROVIDER_MAP.get(provider.upper(), provider.lower())
+    prefix = _resolve_provider_prefix(provider, custom_provider)
     return f"{prefix}/{model_name}"
 
 
@@ -146,14 +151,18 @@ def create_generate_image_tool(
                             "error": f"Image generation config {config_id} not found"
                         }
 
-                    model_string = _build_model_string(
-                        cfg.get("provider", ""),
-                        cfg["model_name"],
-                        cfg.get("custom_provider"),
+                    provider_prefix = _resolve_provider_prefix(
+                        cfg.get("provider", ""), cfg.get("custom_provider")
                     )
+                    model_string = f"{provider_prefix}/{cfg['model_name']}"
                     gen_kwargs["api_key"] = cfg.get("api_key")
-                    if cfg.get("api_base"):
-                        gen_kwargs["api_base"] = cfg["api_base"]
+                    api_base = resolve_api_base(
+                        provider=cfg.get("provider"),
+                        provider_prefix=provider_prefix,
+                        config_api_base=cfg.get("api_base"),
+                    )
+                    if api_base:
+                        gen_kwargs["api_base"] = api_base
                     if cfg.get("api_version"):
                         gen_kwargs["api_version"] = cfg["api_version"]
                     if cfg.get("litellm_params"):
@@ -175,14 +184,18 @@ def create_generate_image_tool(
                             "error": f"Image generation config {config_id} not found"
                         }
 
-                    model_string = _build_model_string(
-                        db_cfg.provider.value,
-                        db_cfg.model_name,
-                        db_cfg.custom_provider,
+                    provider_prefix = _resolve_provider_prefix(
+                        db_cfg.provider.value, db_cfg.custom_provider
                     )
+                    model_string = f"{provider_prefix}/{db_cfg.model_name}"
                     gen_kwargs["api_key"] = db_cfg.api_key
-                    if db_cfg.api_base:
-                        gen_kwargs["api_base"] = db_cfg.api_base
+                    api_base = resolve_api_base(
+                        provider=db_cfg.provider.value,
+                        provider_prefix=provider_prefix,
+                        config_api_base=db_cfg.api_base,
+                    )
+                    if api_base:
+                        gen_kwargs["api_base"] = api_base
                     if db_cfg.api_version:
                         gen_kwargs["api_version"] = db_cfg.api_version
                     if db_cfg.litellm_params:

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

@@ -0,0 +1,41 @@
+from typing import Any
+
+from app.db import SearchSourceConnector
+from app.services.composio_service import ComposioService
+
+
+def split_recipients(value: str | None) -> list[str]:
+    if not value:
+        return []
+    return [recipient.strip() for recipient in value.split(",") if recipient.strip()]
+
+
+def unwrap_composio_data(data: Any) -> Any:
+    if isinstance(data, dict):
+        inner = data.get("data", data)
+        if isinstance(inner, dict):
+            return inner.get("response_data", inner)
+        return inner
+    return data
+
+
+async def execute_composio_gmail_tool(
+    connector: SearchSourceConnector,
+    user_id: str,
+    tool_name: str,
+    params: dict[str, Any],
+) -> tuple[Any, str | None]:
+    cca_id = connector.config.get("composio_connected_account_id")
+    if not cca_id:
+        return None, "Composio connected account ID not found for this Gmail connector."
+
+    result = await ComposioService().execute_tool(
+        connected_account_id=cca_id,
+        tool_name=tool_name,
+        params=params,
+        entity_id=f"surfsense_{user_id}",
+    )
+    if not result.get("success"):
+        return None, result.get("error", "Unknown Composio Gmail error")
+
+    return unwrap_composio_data(result.get("data")), None

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,
@@ -57,246 +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
-            )
-
-            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),
-                    )
+            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
                 )
-                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),
+
+                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": "No Gmail connector found. Please connect Gmail in your workspace settings.",
+                        "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
 
-            logger.info(
-                f"Creating Gmail draft: to='{final_to}', subject='{final_subject}', connector={actual_connector_id}"
-            )
+                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 (
-                connector.connector_type
-                == SearchSourceConnectorType.COMPOSIO_GMAIL_CONNECTOR
-            ):
-                from app.utils.google_credentials import build_composio_credentials
+                if result.rejected:
+                    return {
+                        "status": "rejected",
+                        "message": "User declined. The draft was not created. Do not ask again or suggest alternatives.",
+                    }
 
-                cca_id = connector.config.get("composio_connected_account_id")
-                if cca_id:
-                    creds = build_composio_credentials(cca_id)
+                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": "Selected Gmail connector is invalid or has been disconnected.",
+                        }
+                    actual_connector_id = connector.id
                 else:
-                    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"]
+                    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),
                         )
-                    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,
-                )
-
-            from googleapiclient.discovery import build
-
-            gmail_service = build("gmail", "v1", credentials=creds)
-
-            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:
-                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(
-                        f"Insufficient permissions for connector {actual_connector_id}: {api_err}"
                     )
-                    try:
-                        from sqlalchemy.orm.attributes import flag_modified
+                    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
 
-                        _res = await db_session.execute(
-                            select(SearchSourceConnector).where(
-                                SearchSourceConnector.id == actual_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"]
+                                )
+                            )
+
+                    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.
@@ -32,60 +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.",
-                }
-
-            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()
-                ):
+                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 detail:
+                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 (
+                    _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": "not_found",
-                    "message": f"Email with ID '{message_id}' not found.",
+                    "status": "success",
+                    "message_id": message_id,
+                    "content": content,
                 }
 
-            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__)
 
@@ -39,12 +39,7 @@ def _build_credentials(connector: SearchSourceConnector):
     from app.utils.google_credentials import COMPOSIO_GOOGLE_CONNECTOR_TYPES
 
     if connector.connector_type in COMPOSIO_GOOGLE_CONNECTOR_TYPES:
-        from app.utils.google_credentials import build_composio_credentials
-
-        cca_id = connector.config.get("composio_connected_account_id")
-        if not cca_id:
-            raise ValueError("Composio connected account ID not found.")
-        return build_composio_credentials(cca_id)
+        raise ValueError("Composio connectors must use Composio tool execution.")
 
     from google.oauth2.credentials import Credentials
 
@@ -67,11 +62,85 @@ def _build_credentials(connector: SearchSourceConnector):
     )
 
 
+def _gmail_headers(message: dict[str, Any]) -> dict[str, str]:
+    headers = message.get("payload", {}).get("headers", [])
+    return {
+        header.get("name", "").lower(): header.get("value", "")
+        for header in headers
+        if isinstance(header, dict)
+    }
+
+
+def _format_gmail_summary(message: dict[str, Any]) -> dict[str, Any]:
+    headers = _gmail_headers(message)
+    return {
+        "message_id": message.get("id") or message.get("messageId"),
+        "thread_id": message.get("threadId"),
+        "subject": message.get("subject") or headers.get("subject", "No Subject"),
+        "from": message.get("sender") or headers.get("from", "Unknown"),
+        "to": message.get("to") or headers.get("to", ""),
+        "date": message.get("messageTimestamp") or headers.get("date", ""),
+        "snippet": message.get("snippet") or message.get("messageText", "")[:300],
+        "labels": message.get("labelIds", []),
+    }
+
+
+async def _search_composio_gmail(
+    connector: SearchSourceConnector,
+    user_id: str,
+    query: str,
+    max_results: int,
+) -> dict[str, Any]:
+    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.services.composio_service import ComposioService
+
+    service = ComposioService()
+    messages, _next_token, _estimate, error = await service.get_gmail_messages(
+        connected_account_id=cca_id,
+        entity_id=f"surfsense_{user_id}",
+        query=query,
+        max_results=max_results,
+    )
+    if error:
+        return {"status": "error", "message": error}
+
+    emails = [_format_gmail_summary(message) for message in messages]
+    return {
+        "status": "success",
+        "emails": emails,
+        "total": len(emails),
+        "message": "No emails found." if not emails else None,
+    }
+
+
 def create_search_gmail_tool(
     db_session: AsyncSession | None = None,
     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,
@@ -90,83 +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.",
-                }
-
-            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,
@@ -58,247 +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
-            )
-
-            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),
-                    )
+            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
                 )
-                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),
+
+                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": "No Gmail connector found. Please connect Gmail in your workspace settings.",
+                        "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
 
-            logger.info(
-                f"Sending Gmail email: to='{final_to}', subject='{final_subject}', connector={actual_connector_id}"
-            )
+                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 (
-                connector.connector_type
-                == SearchSourceConnectorType.COMPOSIO_GMAIL_CONNECTOR
-            ):
-                from app.utils.google_credentials import build_composio_credentials
+                if result.rejected:
+                    return {
+                        "status": "rejected",
+                        "message": "User declined. The email was not sent. Do not ask again or suggest alternatives.",
+                    }
 
-                cca_id = connector.config.get("composio_connected_account_id")
-                if cca_id:
-                    creds = build_composio_credentials(cca_id)
+                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": "Selected Gmail connector is invalid or has been disconnected.",
+                        }
+                    actual_connector_id = connector.id
                 else:
-                    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"]
+                    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),
                         )
-                    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,
-                )
-
-            from googleapiclient.discovery import build
-
-            gmail_service = build("gmail", "v1", credentials=creds)
-
-            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:
-                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(
-                        f"Insufficient permissions for connector {actual_connector_id}: {api_err}"
                     )
-                    try:
-                        from sqlalchemy.orm.attributes import flag_modified
+                    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
 
-                        _res = await db_session.execute(
-                            select(SearchSourceConnector).where(
-                                SearchSourceConnector.id == actual_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"]
+                                )
+                            )
+
+                    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,
@@ -55,244 +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}"
-            )
-
-            if (
-                connector.connector_type
-                == SearchSourceConnectorType.COMPOSIO_GMAIL_CONNECTOR
-            ):
-                from app.utils.google_credentials import build_composio_credentials
-
-                cca_id = connector.config.get("composio_connected_account_id")
-                if cca_id:
-                    creds = build_composio_credentials(cca_id)
-                else:
+                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,
                 )
 
-            from googleapiclient.discovery import build
-
-            gmail_service = build("gmail", "v1", credentials=creds)
-
-            try:
-                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,
@@ -76,294 +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}"
-            )
-
-            if (
-                connector.connector_type
-                == SearchSourceConnectorType.COMPOSIO_GMAIL_CONNECTOR
-            ):
-                from app.utils.google_credentials import build_composio_credentials
-
-                cca_id = connector.config.get("composio_connected_account_id")
-                if cca_id:
-                    creds = build_composio_credentials(cca_id)
-                else:
-                    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
                 )
 
-            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)
-
-            # 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}"
-                )
-                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:
-                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
@@ -408,3 +461,35 @@ async def _find_draft_id_by_message(gmail_service: Any, message_id: str) -> str
     except Exception as e:
         logger.warning(f"Failed to look up draft by message_id: {e}")
         return None
+
+
+async def _find_composio_draft_id_by_message(
+    connector: Any, user_id: str, message_id: str
+) -> str | None:
+    from app.agents.new_chat.tools.gmail.composio_helpers import (
+        execute_composio_gmail_tool,
+    )
+
+    page_token = ""
+    while True:
+        params: dict[str, Any] = {
+            "user_id": "me",
+            "max_results": 100,
+            "verbose": False,
+        }
+        if page_token:
+            params["page_token"] = page_token
+
+        data, error = await execute_composio_gmail_tool(
+            connector, user_id, "GMAIL_LIST_DRAFTS", params
+        )
+        if error or not isinstance(data, dict):
+            return None
+
+        for draft in data.get("drafts", []):
+            if draft.get("message", {}).get("id") == message_id:
+                return draft.get("id")
+
+        page_token = data.get("nextPageToken") or data.get("next_page_token") or ""
+        if not page_token:
+            return None

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,
@@ -60,254 +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}"
-            )
-
-            if (
-                connector.connector_type
-                == SearchSourceConnectorType.COMPOSIO_GOOGLE_CALENDAR_CONNECTOR
-            ):
-                from app.utils.google_credentials import build_composio_credentials
-
-                cca_id = connector.config.get("composio_connected_account_id")
-                if cca_id:
-                    creds = build_composio_credentials(cca_id)
-                else:
-                    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,
                 )
 
-            service = await asyncio.get_event_loop().run_in_executor(
-                None, lambda: build("calendar", "v3", credentials=creds)
-            )
+                if result.rejected:
+                    return {
+                        "status": "rejected",
+                        "message": "User declined. The event was not created. Do not ask again or suggest alternatives.",
+                    }
 
-            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()
+                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:
-                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}"
+                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),
+                        )
                     )
-                    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."
+                    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:
-                    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."
+                    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.",
+                        }
+                    actual_connector_id = connector.id
 
-            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}",
-            }
+                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,
+                    )
+
+                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,
@@ -54,240 +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}"
-            )
-
-            if (
-                connector.connector_type
-                == SearchSourceConnectorType.COMPOSIO_GOOGLE_CALENDAR_CONNECTOR
-            ):
-                from app.utils.google_credentials import build_composio_credentials
-
-                cca_id = connector.config.get("composio_connected_account_id")
-                if cca_id:
-                    creds = build_composio_credentials(cca_id)
-                else:
+                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,
                 )
 
-            service = await asyncio.get_event_loop().run_in_executor(
-                None, lambda: build("calendar", "v3", credentials=creds)
-            )
-
-            try:
-                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__)
 
@@ -16,11 +16,57 @@ _CALENDAR_TYPES = [
 ]
 
 
+def _to_calendar_boundary(value: str, *, is_end: bool) -> str:
+    if "T" in value:
+        return value
+    time = "23:59:59" if is_end else "00:00:00"
+    return f"{value}T{time}Z"
+
+
+def _format_calendar_events(events_raw: list[dict[str, Any]]) -> list[dict[str, Any]]:
+    events = []
+    for ev in events_raw:
+        start = ev.get("start", {})
+        end = ev.get("end", {})
+        attendees_raw = ev.get("attendees", [])
+        events.append(
+            {
+                "event_id": ev.get("id"),
+                "summary": ev.get("summary", "No Title"),
+                "start": start.get("dateTime") or start.get("date", ""),
+                "end": end.get("dateTime") or end.get("date", ""),
+                "location": ev.get("location", ""),
+                "description": ev.get("description", ""),
+                "html_link": ev.get("htmlLink", ""),
+                "attendees": [a.get("email", "") for a in attendees_raw[:10]],
+                "status": ev.get("status", ""),
+            }
+        )
+    return events
+
+
 def create_search_calendar_events_tool(
     db_session: AsyncSession | None = None,
     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,
@@ -38,7 +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.",
@@ -47,76 +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.",
-                }
+                connector = result.scalars().first()
+                if not connector:
+                    return {
+                        "status": "error",
+                        "message": "No Google Calendar connector found. Please connect Google Calendar in your workspace settings.",
+                    }
 
-            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 = []
-            for ev in events_raw:
-                start = ev.get("start", {})
-                end = ev.get("end", {})
-                attendees_raw = ev.get("attendees", [])
-                events.append(
-                    {
-                        "event_id": ev.get("id"),
-                        "summary": ev.get("summary", "No Title"),
-                        "start": start.get("dateTime") or start.get("date", ""),
-                        "end": end.get("dateTime") or end.get("date", ""),
-                        "location": ev.get("location", ""),
-                        "description": ev.get("description", ""),
-                        "html_link": ev.get("htmlLink", ""),
-                        "attendees": [a.get("email", "") for a in attendees_raw[:10]],
-                        "status": ev.get("status", ""),
-                    }
-                )
+                    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,
@@ -74,272 +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",
+                    }
 
-            if (
-                connector.connector_type
-                == SearchSourceConnectorType.COMPOSIO_GOOGLE_CALENDAR_CONNECTOR
-            ):
-                from app.utils.google_credentials import build_composio_credentials
+                event = context["event"]
+                event_id = event["event_id"]
+                document_id = event.get("document_id")
+                connector_id_from_context = context["account"]["id"]
 
-                cca_id = connector.config.get("composio_connected_account_id")
-                if cca_id:
-                    creds = build_composio_credentials(cca_id)
-                else:
+                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,
                 )
 
-            service = await asyncio.get_event_loop().run_in_executor(
-                None, lambda: build("calendar", "v3", credentials=creds)
-            )
+                if result.rejected:
+                    return {
+                        "status": "rejected",
+                        "message": "User declined. The event was not updated. Do not ask again or suggest alternatives.",
+                    }
 
-            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
+                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:
-                updated = await asyncio.get_event_loop().run_in_executor(
-                    None,
-                    lambda: (
-                        service.events()
-                        .patch(
-                            calendarId="primary",
-                            eventId=final_event_id,
-                            body=update_body,
-                        )
-                        .execute()
-                    ),
+                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),
+                    )
                 )
-            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.",
@@ -78,195 +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
-            )
+            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
+                )
 
-            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),
+                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 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
+                    return {"status": "error", "message": context["error"]}
 
-            logger.info(
-                f"Creating Google Drive file: name='{final_name}', type='{final_file_type}', connector={actual_connector_id}"
-            )
-
-            pre_built_creds = None
-            if (
-                connector.connector_type
-                == SearchSourceConnectorType.COMPOSIO_GOOGLE_DRIVE_CONNECTOR
-            ):
-                from app.utils.google_credentials import build_composio_credentials
-
-                cca_id = connector.config.get("composio_connected_account_id")
-                if cca_id:
-                    pre_built_creds = build_composio_credentials(cca_id)
-
-            client = GoogleDriveClient(
-                session=db_session,
-                connector_id=actual_connector_id,
-                credentials=pre_built_creds,
-            )
-            try:
-                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,
@@ -55,197 +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.",
-                }
-
-            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,
-            )
-
-            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}"
-            )
-
-            pre_built_creds = None
-            if (
-                connector.connector_type
-                == SearchSourceConnectorType.COMPOSIO_GOOGLE_DRIVE_CONNECTOR
-            ):
-                from app.utils.google_credentials import build_composio_credentials
-
-                cca_id = connector.config.get("composio_connected_account_id")
-                if cca_id:
-                    pre_built_creds = build_composio_credentials(cca_id)
-
-            client = GoogleDriveClient(
-                session=db_session,
-                connector_id=connector.id,
-                credentials=pre_built_creds,
-            )
-            try:
-                await client.trash_file(file_id=final_file_id)
-            except HttpError as http_err:
-                if http_err.resp.status == 403:
+                account = context.get("account", {})
+                if account.get("auth_expired"):
                     logger.warning(
-                        f"Insufficient permissions for connector {connector.id}: {http_err}"
+                        "Google Drive 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 Google Drive account needs additional permissions. Please re-authenticate in connector settings.",
+                        "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",
                     }
-                raise
 
-            logger.info(
-                f"Google Drive file deleted (moved to trash): file_id={final_file_id}"
-            )
+                file = context["file"]
+                file_id = file["file_id"]
+                document_id = file.get("document_id")
+                connector_id_from_context = context["account"]["id"]
 
-            trash_result: dict[str, Any] = {
-                "status": "success",
-                "file_id": final_file_id,
-                "message": f"Successfully moved '{file['name']}' to trash.",
-            }
+                if not file_id:
+                    return {
+                        "status": "error",
+                        "message": "File ID is missing from the indexed document. Please re-index the file and try again.",
+                    }
 
-            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/hitl.py

@@ -50,6 +50,7 @@ DEFAULT_AUTO_APPROVED_TOOLS: frozenset[str] = frozenset(
     {
         "create_gmail_draft",
         "update_gmail_draft",
+        "create_calendar_event",
         "create_notion_page",
         "create_confluence_page",
         "create_google_drive_file",

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}",