diff --git a/surfsense_backend/app/agents/multi_agent_chat/main_agent/runtime/factory.py b/surfsense_backend/app/agents/multi_agent_chat/main_agent/runtime/factory.py
index b2b553b83..8451b3b7d 100644
--- a/surfsense_backend/app/agents/multi_agent_chat/main_agent/runtime/factory.py
+++ b/surfsense_backend/app/agents/multi_agent_chat/main_agent/runtime/factory.py
@@ -29,7 +29,10 @@ from app.agents.new_chat.tools.invalid_tool import INVALID_TOOL_NAME, invalid_to
 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.services.user_tool_allowlist import fetch_user_allowlist_rulesets
+from app.services.user_tool_allowlist import (
+    fetch_user_allowlist_rulesets,
+    make_trusted_tool_saver,
+)
 from app.utils.perf import get_perf_logger
 
 from ..system_prompt import build_main_agent_system_prompt
@@ -153,28 +156,37 @@ async def create_multi_agent_chat_deep_agent(
     # ``ask`` via last-match-wins. Anonymous turns and read failures both
     # degrade to "no user rules" rather than blocking the turn.
     user_allowlist_by_subagent: dict[str, Any] = {}
+    trusted_tool_saver = None
     if user_id:
-        _t0 = time.perf_counter()
         try:
             import uuid as _uuid
 
-            user_allowlist_by_subagent = await fetch_user_allowlist_rulesets(
-                db_session,
-                user_id=_uuid.UUID(user_id),
-                search_space_id=search_space_id,
+            user_uuid = _uuid.UUID(user_id)
+        except (TypeError, ValueError):
+            user_uuid = None
+
+        if user_uuid is not None:
+            _t0 = time.perf_counter()
+            try:
+                user_allowlist_by_subagent = await fetch_user_allowlist_rulesets(
+                    db_session,
+                    user_id=user_uuid,
+                    search_space_id=search_space_id,
+                )
+            except Exception as e:
+                logging.warning(
+                    "User allow-list fetch failed; subagents will run without user trust rules this turn: %s",
+                    e,
+                )
+                user_allowlist_by_subagent = {}
+            _perf_log.info(
+                "[create_agent] fetch_user_allowlist_rulesets in %.3fs (%d subagents have rules)",
+                time.perf_counter() - _t0,
+                len(user_allowlist_by_subagent),
             )
-        except Exception as e:
-            logging.warning(
-                "User allow-list fetch failed; subagents will run without user trust rules this turn: %s",
-                e,
-            )
-            user_allowlist_by_subagent = {}
-        _perf_log.info(
-            "[create_agent] fetch_user_allowlist_rulesets in %.3fs (%d subagents have rules)",
-            time.perf_counter() - _t0,
-            len(user_allowlist_by_subagent),
-        )
+            trusted_tool_saver = make_trusted_tool_saver(user_uuid)
     dependencies["user_allowlist_by_subagent"] = user_allowlist_by_subagent
+    dependencies["trusted_tool_saver"] = trusted_tool_saver
 
     modified_disabled_tools = list(disabled_tools) if disabled_tools else []
 
diff --git a/surfsense_backend/app/agents/multi_agent_chat/middleware/shared/permissions/middleware/core.py b/surfsense_backend/app/agents/multi_agent_chat/middleware/shared/permissions/middleware/core.py
index a96fca7dd..f5c8e040c 100644
--- a/surfsense_backend/app/agents/multi_agent_chat/middleware/shared/permissions/middleware/core.py
+++ b/surfsense_backend/app/agents/multi_agent_chat/middleware/shared/permissions/middleware/core.py
@@ -9,31 +9,12 @@ This middleware layers OpenCode's wildcard-ruleset model on top of the
 unified langchain HITL wire format (see :mod:`hitl_wire`), so it sits
 beside ``HumanInTheLoopMiddleware`` and self-gated approvals on a single
 parallel-HITL routing layer in ``task_tool`` + ``resume_routing``.
-
-Per-tool-call flow inside :meth:`_process`:
-
-1. Skip when the last message has no tool calls.
-2. For each call, evaluate the rules. ``deny`` is replaced with a
-   synthetic :class:`ToolMessage` carrying a typed
-   :class:`StreamingError`. ``ask`` raises an interrupt via
-   :mod:`interrupt.request`; the resulting decision is dispatched here:
-
-   - ``once``  → keep the call as-is.
-   - ``always`` → also extend the runtime ruleset.
-   - ``reject`` (with feedback) → :class:`CorrectedError`.
-   - ``reject`` (no feedback)   → :class:`RejectedError`.
-
-   ``allow`` keeps the call unchanged.
-
-3. Returns an updated ``AIMessage`` (tool calls minus the denied ones)
-   plus any deny ``ToolMessage`` entries appended after it. Tool-list
-   filtering at ``before_model`` is intentionally not done here — that
-   would invalidate provider prompt-cache prefixes.
 """
 
 from __future__ import annotations
 
 import logging
+from dataclasses import dataclass
 from typing import Any
 
 from langchain.agents.middleware.types import (
@@ -47,6 +28,7 @@ from langgraph.runtime import Runtime
 
 from app.agents.new_chat.errors import CorrectedError, RejectedError
 from app.agents.new_chat.permissions import Ruleset
+from app.services.user_tool_allowlist import TrustedToolSaver
 
 from ..ask.edit import merge_edited_args
 from ..ask.request import request_permission_decision
@@ -59,6 +41,14 @@ from .runtime_promote import persist_always
 logger = logging.getLogger(__name__)
 
 
+@dataclass(frozen=True)
+class _AlwaysPromotion:
+    """A pending request to save an ``always`` decision to the user's trust list."""
+
+    connector_id: int
+    tool_name: str
+
+
 class PermissionMiddleware(AgentMiddleware):  # type: ignore[type-arg]
     """Allow/deny/ask layer over the agent's tool calls.
 
@@ -76,6 +66,10 @@ class PermissionMiddleware(AgentMiddleware):  # type: ignore[type-arg]
         tools_by_name: Map from tool name to :class:`BaseTool`, used to
             decorate ``ask`` interrupts with the tool's description and
             MCP metadata for the FE card.
+        trusted_tool_saver: Async callback invoked on ``always`` decisions
+            for MCP tools (those whose ``metadata`` carries an
+            ``mcp_connector_id``). Without it the promotion only lives
+            in-memory for the current agent instance.
     """
 
     tools = ()
@@ -88,6 +82,7 @@ class PermissionMiddleware(AgentMiddleware):  # type: ignore[type-arg]
         runtime_ruleset: Ruleset | None = None,
         always_emit_interrupt_payload: bool = True,
         tools_by_name: dict[str, BaseTool] | None = None,
+        trusted_tool_saver: TrustedToolSaver | None = None,
     ) -> None:
         super().__init__()
         self._static_rulesets: list[Ruleset] = list(rulesets or [])
@@ -99,23 +94,31 @@ class PermissionMiddleware(AgentMiddleware):  # type: ignore[type-arg]
         )
         self._emit_interrupt = always_emit_interrupt_payload
         self._tools_by_name: dict[str, BaseTool] = dict(tools_by_name or {})
+        self._trusted_tool_saver: TrustedToolSaver | None = trusted_tool_saver
 
     def _process(
         self,
         state: AgentState,
         runtime: Runtime[Any],
-    ) -> dict[str, Any] | None:
+    ) -> tuple[dict[str, Any] | None, list[_AlwaysPromotion]]:
+        """Pure decision pass: returns ``(state_update, pending_promotions)``.
+
+        Side effects performed here are in-memory only (rule promotion
+        into ``runtime_ruleset``). DB writes for ``always`` decisions
+        are queued as ``_AlwaysPromotion`` and flushed by the async hook.
+        """
         del runtime
         messages = state.get("messages") or []
         if not messages:
-            return None
+            return None, []
         last = messages[-1]
         if not isinstance(last, AIMessage) or not last.tool_calls:
-            return None
+            return None, []
 
         rulesets = all_rulesets(self._static_rulesets, self._runtime_ruleset)
         deny_messages: list[ToolMessage] = []
         kept_calls: list[dict[str, Any]] = []
+        promotions: list[_AlwaysPromotion] = []
         any_change = False
 
         for raw in last.tool_calls:
@@ -162,6 +165,9 @@ class PermissionMiddleware(AgentMiddleware):  # type: ignore[type-arg]
                         any_change = True
                     if kind == "always":
                         persist_always(self._runtime_ruleset, name, patterns)
+                        promotion = self._build_always_promotion(name)
+                        if promotion is not None:
+                            promotions.append(promotion)
                     kept_calls.append(final_call)
                 elif kind == "reject":
                     feedback = decision.get("feedback")
@@ -180,23 +186,39 @@ class PermissionMiddleware(AgentMiddleware):  # type: ignore[type-arg]
             kept_calls.append(call)
 
         if not any_change and len(kept_calls) == len(last.tool_calls):
-            return None
+            return None, promotions
 
         updated = last.model_copy(update={"tool_calls": kept_calls})
         result_messages: list[Any] = [updated]
         if deny_messages:
             result_messages.extend(deny_messages)
-        return {"messages": result_messages}
+        return {"messages": result_messages}, promotions
+
+    def _build_always_promotion(self, tool_name: str) -> _AlwaysPromotion | None:
+        """Return a save request iff the tool exposes an ``mcp_connector_id``."""
+        tool = self._tools_by_name.get(tool_name)
+        metadata = getattr(tool, "metadata", None) or {}
+        connector_id = metadata.get("mcp_connector_id")
+        if not isinstance(connector_id, int):
+            return None
+        return _AlwaysPromotion(connector_id=connector_id, tool_name=tool_name)
 
     def after_model(  # type: ignore[override]
         self, state: AgentState, runtime: Runtime[ContextT]
     ) -> dict[str, Any] | None:
-        return self._process(state, runtime)
+        update, _ = self._process(state, runtime)
+        return update
 
     async def aafter_model(  # type: ignore[override]
         self, state: AgentState, runtime: Runtime[ContextT]
     ) -> dict[str, Any] | None:
-        return self._process(state, runtime)
+        update, promotions = self._process(state, runtime)
+        if self._trusted_tool_saver is not None:
+            for promotion in promotions:
+                await self._trusted_tool_saver(
+                    promotion.connector_id, promotion.tool_name
+                )
+        return update
 
 
 __all__ = ["PermissionMiddleware"]
diff --git a/surfsense_backend/app/agents/multi_agent_chat/middleware/shared/permissions/middleware/factory.py b/surfsense_backend/app/agents/multi_agent_chat/middleware/shared/permissions/middleware/factory.py
index 9642e2664..3c061ded6 100644
--- a/surfsense_backend/app/agents/multi_agent_chat/middleware/shared/permissions/middleware/factory.py
+++ b/surfsense_backend/app/agents/multi_agent_chat/middleware/shared/permissions/middleware/factory.py
@@ -29,6 +29,7 @@ from langchain_core.tools import BaseTool
 
 from app.agents.new_chat.feature_flags import AgentFeatureFlags
 from app.agents.new_chat.permissions import Rule, Ruleset
+from app.services.user_tool_allowlist import TrustedToolSaver
 
 from .core import PermissionMiddleware
 
@@ -43,6 +44,7 @@ def build_permission_mw(
     flags: AgentFeatureFlags,
     subagent_rulesets: list[Ruleset] | None = None,
     tools: Sequence[BaseTool] | None = None,
+    trusted_tool_saver: TrustedToolSaver | None = None,
 ) -> PermissionMiddleware | None:
     """Return a configured :class:`PermissionMiddleware` or ``None`` when no work is needed.
 
@@ -58,6 +60,9 @@ def build_permission_mw(
             an explicit ``ask`` rule always asks.
         tools: Subagent tools used to decorate ``ask`` interrupts with
             FE-card metadata (description, MCP connector). Optional.
+        trusted_tool_saver: Async callback invoked when an MCP tool's
+            ``always`` decision lands; persists the user's preference to
+            ``connector.config['trusted_tools']``. Optional.
 
     Returns:
         ``None`` when the engine has no rules to enforce
@@ -73,7 +78,11 @@ def build_permission_mw(
     if subagent_rulesets:
         rulesets.extend(subagent_rulesets)
     tools_by_name = {t.name: t for t in (tools or [])}
-    return PermissionMiddleware(rulesets=rulesets, tools_by_name=tools_by_name)
+    return PermissionMiddleware(
+        rulesets=rulesets,
+        tools_by_name=tools_by_name,
+        trusted_tool_saver=trusted_tool_saver,
+    )
 
 
 __all__ = ["build_permission_mw"]
diff --git a/surfsense_backend/app/agents/multi_agent_chat/subagents/builtins/knowledge_base/middleware_stack.py b/surfsense_backend/app/agents/multi_agent_chat/subagents/builtins/knowledge_base/middleware_stack.py
index e6c969678..778bb250c 100644
--- a/surfsense_backend/app/agents/multi_agent_chat/subagents/builtins/knowledge_base/middleware_stack.py
+++ b/surfsense_backend/app/agents/multi_agent_chat/subagents/builtins/knowledge_base/middleware_stack.py
@@ -93,7 +93,11 @@ def build_kb_middleware(
         user_allowlist = _kb_user_allowlist(dependencies, subagent_name)
         if user_allowlist is not None:
             rulesets.append(user_allowlist)
-        permission_mw = build_permission_mw(flags=flags, subagent_rulesets=rulesets)
+        permission_mw = build_permission_mw(
+            flags=flags,
+            subagent_rulesets=rulesets,
+            trusted_tool_saver=dependencies.get("trusted_tool_saver"),
+        )
     return [
         mws["todos"],
         build_kb_context_projection_mw(),
diff --git a/surfsense_backend/app/agents/multi_agent_chat/subagents/shared/subagent_builder.py b/surfsense_backend/app/agents/multi_agent_chat/subagents/shared/subagent_builder.py
index 3d1fa1504..7173901f9 100644
--- a/surfsense_backend/app/agents/multi_agent_chat/subagents/shared/subagent_builder.py
+++ b/surfsense_backend/app/agents/multi_agent_chat/subagents/shared/subagent_builder.py
@@ -74,7 +74,10 @@ def pack_subagent(
     if user_allowlist is not None:
         subagent_rulesets.append(user_allowlist)
     per_subagent_perm = build_permission_mw(
-        flags=flags, subagent_rulesets=subagent_rulesets, tools=tools
+        flags=flags,
+        subagent_rulesets=subagent_rulesets,
+        tools=tools,
+        trusted_tool_saver=dependencies.get("trusted_tool_saver"),
     )
 
     prepended: list[Any] = []
diff --git a/surfsense_backend/app/services/user_tool_allowlist.py b/surfsense_backend/app/services/user_tool_allowlist.py
index 83b075fb7..fb21a7df2 100644
--- a/surfsense_backend/app/services/user_tool_allowlist.py
+++ b/surfsense_backend/app/services/user_tool_allowlist.py
@@ -1,33 +1,16 @@
-"""User-scoped tool allow-list backed by ``SearchSourceConnector.config``.
+"""User-scoped trusted-tools list backed by ``SearchSourceConnector.config``.
 
-Stores the user's "always allow" preferences as a list of tool names under
-``connector.config['trusted_tools']``. Storage is per
-``(user_id, search_space_id, connector_id)`` — i.e. tied to a specific
-connected account inside a specific workspace, exactly what the UI cares
-about.
-
-Callers split into two roles:
-
-- **Writers** — the ``/connectors/.../trust-tool`` and ``/untrust-tool``
-  HTTP routes, and the chat resume handler when it processes a
-  ``{type: "always"}`` decision. Both call
-  :func:`add_user_trust` / :func:`remove_user_trust`. The FE button is
-  the upstream UI trigger but it talks to the routes, never to this
-  module directly.
-- **Reader** — the subagent compile path, which calls
-  :func:`fetch_user_allowlist_rulesets` and layers the result after the
-  subagent's coded ruleset. User ``allow`` rules then override coded
-  ``ask`` via the rule engine's last-match-wins evaluation.
-
-Coded ``deny`` rules are intentionally **not** overridable by this
-allow-list — only ``ask`` can be promoted to ``allow``. The rule engine
-enforces this naturally because user rules only ever emit ``allow``.
+Storage is per ``(user_id, search_space_id, connector_id)`` under
+``connector.config['trusted_tools']``. The list only ever encodes
+``allow`` decisions; coded ``deny`` rules cannot be overridden here.
 """
 
 from __future__ import annotations
 
+import logging
 import uuid
 from collections import defaultdict
+from collections.abc import Awaitable, Callable
 
 from sqlalchemy import select
 from sqlalchemy.ext.asyncio import AsyncSession
@@ -37,10 +20,14 @@ from app.agents.multi_agent_chat.constants import (
     CONNECTOR_TYPE_TO_CONNECTOR_AGENT_MAPS,
 )
 from app.agents.new_chat.permissions import Rule, Ruleset
-from app.db import SearchSourceConnector
+from app.db import SearchSourceConnector, async_session_maker
+
+logger = logging.getLogger(__name__)
 
 _TRUSTED_TOOLS_KEY = "trusted_tools"
 
+TrustedToolSaver = Callable[[int, str], Awaitable[None]]
+
 
 async def _load_owned_connector(
     session: AsyncSession,
@@ -48,11 +35,7 @@ async def _load_owned_connector(
     user_id: uuid.UUID,
     connector_id: int,
 ) -> SearchSourceConnector | None:
-    """Return a connector iff it belongs to ``user_id``, else ``None``.
-
-    Ownership scoping is mandatory: the trust list mutates user-private
-    data, callers must never write across user boundaries.
-    """
+    """Return the connector iff owned by ``user_id``, else ``None``."""
     result = await session.execute(
         select(SearchSourceConnector).where(
             SearchSourceConnector.id == connector_id,
@@ -84,11 +67,7 @@ async def add_user_trust(
     connector_id: int,
     tool_name: str,
 ) -> list[str]:
-    """Append ``tool_name`` to the connector's trusted list (idempotent).
-
-    Returns the updated trusted-tools list. Raises ``LookupError`` when
-    the connector does not exist or is not owned by ``user_id``.
-    """
+    """Append ``tool_name`` to the connector's trusted list; raise ``LookupError`` if not owned."""
     connector = await _load_owned_connector(
         session, user_id=user_id, connector_id=connector_id
     )
@@ -112,11 +91,7 @@ async def remove_user_trust(
     connector_id: int,
     tool_name: str,
 ) -> list[str]:
-    """Remove ``tool_name`` from the connector's trusted list (idempotent).
-
-    Returns the updated trusted-tools list. Raises ``LookupError`` when
-    the connector does not exist or is not owned by ``user_id``.
-    """
+    """Remove ``tool_name`` from the connector's trusted list; raise ``LookupError`` if not owned."""
     connector = await _load_owned_connector(
         session, user_id=user_id, connector_id=connector_id
     )
@@ -139,20 +114,10 @@ async def fetch_user_allowlist_rulesets(
     user_id: uuid.UUID,
     search_space_id: int,
 ) -> dict[str, Ruleset]:
-    """Project the user's trusted-tool lists into per-subagent rulesets.
+    """Project the user's trusted tools into per-subagent ``allow`` rulesets.
 
-    Walks every connector the user owns in this workspace, maps each
-    ``connector_type`` to its consuming subagent via
-    :data:`CONNECTOR_TYPE_TO_CONNECTOR_AGENT_MAPS`, and emits one
-    ``Rule(permission=tool_name, pattern="*", action="allow")`` per
-    trusted entry. Rules from different connector accounts feeding the
-    same subagent (e.g. two Linear workspaces) are merged into one
-    ruleset; duplicates are harmless under last-match-wins.
-
-    Connectors whose type is not mapped (search APIs, Github, etc.) and
-    connectors with empty trust lists contribute nothing. Subagents
-    with no trusted tools are absent from the returned dict — callers
-    should treat ``missing == empty``.
+    Subagents with no trusted tools are absent from the result —
+    callers must treat ``missing == empty``.
     """
     result = await session.execute(
         select(
@@ -189,8 +154,35 @@ async def fetch_user_allowlist_rulesets(
     }
 
 
+def make_trusted_tool_saver(user_id: uuid.UUID) -> TrustedToolSaver:
+    """Bind ``user_id`` into a saver closure; failures are logged, never raised."""
+
+    async def trusted_tool_saver(connector_id: int, tool_name: str) -> None:
+        try:
+            async with async_session_maker() as session:
+                await add_user_trust(
+                    session,
+                    user_id=user_id,
+                    connector_id=connector_id,
+                    tool_name=tool_name,
+                )
+                await session.commit()
+        except LookupError as exc:
+            logger.warning("trusted-tool save skipped: %s", exc)
+        except Exception:
+            logger.exception(
+                "trusted-tool save failed for connector=%s tool=%s",
+                connector_id,
+                tool_name,
+            )
+
+    return trusted_tool_saver
+
+
 __all__ = [
+    "TrustedToolSaver",
     "add_user_trust",
     "fetch_user_allowlist_rulesets",
+    "make_trusted_tool_saver",
     "remove_user_trust",
 ]
diff --git a/surfsense_backend/tests/unit/agents/multi_agent_chat/middleware/shared/permissions/test_permission_ask_mcp_context.py b/surfsense_backend/tests/unit/agents/multi_agent_chat/middleware/shared/permissions/test_permission_ask_mcp_context.py
index b6768c530..f70f027a9 100644
--- a/surfsense_backend/tests/unit/agents/multi_agent_chat/middleware/shared/permissions/test_permission_ask_mcp_context.py
+++ b/surfsense_backend/tests/unit/agents/multi_agent_chat/middleware/shared/permissions/test_permission_ask_mcp_context.py
@@ -128,7 +128,7 @@ def _emit_tool_call(tool_name: str, args: dict[str, Any], call_id: str):
 
 def _compile_graph_with(pm, tool_name: str, args: dict[str, Any], call_id: str):
     def after(state: _State) -> dict[str, Any] | None:
-        return pm._process(state, None)  # type: ignore[arg-type]
+        return pm.after_model(state, None)  # type: ignore[arg-type]
 
     g = StateGraph(_State)
     g.add_node("emit", _emit_tool_call(tool_name, args, call_id))
diff --git a/surfsense_backend/tests/unit/agents/multi_agent_chat/middleware/shared/permissions/test_subagent_owned_ruleset.py b/surfsense_backend/tests/unit/agents/multi_agent_chat/middleware/shared/permissions/test_subagent_owned_ruleset.py
index 6f3f34536..6406fb09a 100644
--- a/surfsense_backend/tests/unit/agents/multi_agent_chat/middleware/shared/permissions/test_subagent_owned_ruleset.py
+++ b/surfsense_backend/tests/unit/agents/multi_agent_chat/middleware/shared/permissions/test_subagent_owned_ruleset.py
@@ -84,9 +84,7 @@ def _build_graph_with_permission_middleware(
     def after_node(state: _State) -> dict[str, Any] | None:
         if pm is None:
             return None
-        # PermissionMiddleware._process ignores runtime; the test never relies
-        # on the runtime context, so passing None keeps the harness lean.
-        return pm._process(state, None)  # type: ignore[arg-type]
+        return pm.after_model(state, None)  # type: ignore[arg-type]
 
     g = StateGraph(_State)
     g.add_node("emit", node)
diff --git a/surfsense_backend/tests/unit/agents/multi_agent_chat/middleware/shared/permissions/test_trusted_tool_save_on_always.py b/surfsense_backend/tests/unit/agents/multi_agent_chat/middleware/shared/permissions/test_trusted_tool_save_on_always.py
new file mode 100644
index 000000000..8b469a2cb
--- /dev/null
+++ b/surfsense_backend/tests/unit/agents/multi_agent_chat/middleware/shared/permissions/test_trusted_tool_save_on_always.py
@@ -0,0 +1,180 @@
+"""``always`` decisions for MCP tools are saved via the trusted-tool saver."""
+
+from __future__ import annotations
+
+from typing import Annotated, Any
+
+import pytest
+from langchain_core.messages import AIMessage, HumanMessage
+from langchain_core.tools import StructuredTool
+from langgraph.checkpoint.memory import InMemorySaver
+from langgraph.graph import END, START, StateGraph
+from langgraph.graph.message import add_messages
+from langgraph.types import Command
+from pydantic import BaseModel
+from typing_extensions import TypedDict
+
+from app.agents.multi_agent_chat.middleware.shared.permissions import (
+    build_permission_mw,
+)
+from app.agents.new_chat.feature_flags import AgentFeatureFlags
+from app.agents.new_chat.permissions import Rule, Ruleset
+
+
+class _NoArgs(BaseModel):
+    pass
+
+
+async def _noop(**_kwargs) -> str:
+    return ""
+
+
+def _ask_rule(tool_name: str) -> Rule:
+    return Rule(permission=tool_name, pattern="*", action="ask")
+
+
+def _make_mcp_tool(*, name: str, connector_id: int):
+    return StructuredTool(
+        name=name,
+        description=f"Run {name} via MCP.",
+        coroutine=_noop,
+        args_schema=_NoArgs,
+        metadata={
+            "mcp_connector_id": connector_id,
+            "mcp_connector_name": "Linear",
+            "mcp_transport": "http",
+            "hitl": True,
+        },
+    )
+
+
+def _make_native_tool(*, name: str):
+    return StructuredTool(
+        name=name,
+        description=f"Native {name}.",
+        coroutine=_noop,
+        args_schema=_NoArgs,
+        metadata={"hitl": True},
+    )
+
+
+class _State(TypedDict, total=False):
+    messages: Annotated[list, add_messages]
+
+
+def _build_graph(pm, tool_name: str):
+    def emit(_state: _State) -> dict[str, Any]:
+        return {
+            "messages": [
+                AIMessage(
+                    content="",
+                    tool_calls=[
+                        {
+                            "name": tool_name,
+                            "args": {},
+                            "id": "call-1",
+                            "type": "tool_call",
+                        }
+                    ],
+                )
+            ]
+        }
+
+    g = StateGraph(_State)
+    g.add_node("emit", emit)
+    g.add_node("permission", pm.aafter_model)  # type: ignore[arg-type]
+    g.add_edge(START, "emit")
+    g.add_edge("emit", "permission")
+    g.add_edge("permission", END)
+    return g.compile(checkpointer=InMemorySaver())
+
+
+@pytest.mark.asyncio
+async def test_always_decision_saves_mcp_tool_via_callback():
+    saved: list[tuple[int, str]] = []
+
+    async def trusted_tool_saver(connector_id: int, tool_name: str) -> None:
+        saved.append((connector_id, tool_name))
+
+    tool = _make_mcp_tool(name="linear_create_issue", connector_id=7)
+    pm = build_permission_mw(
+        flags=AgentFeatureFlags(enable_permission=False),
+        subagent_rulesets=[Ruleset(origin="linear", rules=[_ask_rule(tool.name)])],
+        tools=[tool],
+        trusted_tool_saver=trusted_tool_saver,
+    )
+    assert pm is not None
+
+    graph = _build_graph(pm, tool.name)
+    config = {"configurable": {"thread_id": "always-mcp"}}
+    await graph.ainvoke({"messages": [HumanMessage(content="seed")]}, config)
+    await graph.ainvoke(Command(resume={"decisions": [{"type": "always"}]}), config)
+
+    assert saved == [(7, "linear_create_issue")]
+
+
+@pytest.mark.asyncio
+async def test_once_decision_does_not_save():
+    saved: list[tuple[int, str]] = []
+
+    async def trusted_tool_saver(connector_id: int, tool_name: str) -> None:
+        saved.append((connector_id, tool_name))
+
+    tool = _make_mcp_tool(name="linear_create_issue", connector_id=7)
+    pm = build_permission_mw(
+        flags=AgentFeatureFlags(enable_permission=False),
+        subagent_rulesets=[Ruleset(origin="linear", rules=[_ask_rule(tool.name)])],
+        tools=[tool],
+        trusted_tool_saver=trusted_tool_saver,
+    )
+    assert pm is not None
+
+    graph = _build_graph(pm, tool.name)
+    config = {"configurable": {"thread_id": "once-mcp"}}
+    await graph.ainvoke({"messages": [HumanMessage(content="seed")]}, config)
+    await graph.ainvoke(Command(resume={"decisions": [{"type": "approve"}]}), config)
+
+    assert saved == []
+
+
+@pytest.mark.asyncio
+async def test_always_decision_for_native_tool_skips_save():
+    """Native tools have no ``mcp_connector_id`` so there is nowhere to persist trust."""
+    saved: list[tuple[int, str]] = []
+
+    async def trusted_tool_saver(connector_id: int, tool_name: str) -> None:
+        saved.append((connector_id, tool_name))
+
+    tool = _make_native_tool(name="rm")
+    pm = build_permission_mw(
+        flags=AgentFeatureFlags(enable_permission=False),
+        subagent_rulesets=[Ruleset(origin="kb", rules=[_ask_rule(tool.name)])],
+        tools=[tool],
+        trusted_tool_saver=trusted_tool_saver,
+    )
+    assert pm is not None
+
+    graph = _build_graph(pm, tool.name)
+    config = {"configurable": {"thread_id": "always-native"}}
+    await graph.ainvoke({"messages": [HumanMessage(content="seed")]}, config)
+    await graph.ainvoke(Command(resume={"decisions": [{"type": "always"}]}), config)
+
+    assert saved == []
+
+
+@pytest.mark.asyncio
+async def test_always_decision_with_no_saver_callback_is_a_noop():
+    """Anonymous turns build the middleware without a ``trusted_tool_saver``; must not crash."""
+    tool = _make_mcp_tool(name="linear_create_issue", connector_id=7)
+    pm = build_permission_mw(
+        flags=AgentFeatureFlags(enable_permission=False),
+        subagent_rulesets=[Ruleset(origin="linear", rules=[_ask_rule(tool.name)])],
+        tools=[tool],
+        trusted_tool_saver=None,
+    )
+    assert pm is not None
+
+    graph = _build_graph(pm, tool.name)
+    config = {"configurable": {"thread_id": "anon-always"}}
+    await graph.ainvoke({"messages": [HumanMessage(content="seed")]}, config)
+    await graph.ainvoke(Command(resume={"decisions": [{"type": "always"}]}), config)