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 6002eb3c2..b2b553b83 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
@@ -29,6 +29,7 @@ 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.utils.perf import get_perf_logger
 
 from ..system_prompt import build_main_agent_system_prompt
@@ -146,6 +147,35 @@ async def create_multi_agent_chat_deep_agent(
         len(mcp_tools_by_agent),
     )
 
+    # User-scoped allow-list ("Always Allow" persisted to
+    # ``SearchSourceConnector.config.trusted_tools``). Layered last in each
+    # subagent's PermissionMiddleware so user ``allow`` overrides coded
+    # ``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] = {}
+    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,
+            )
+        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),
+        )
+    dependencies["user_allowlist_by_subagent"] = user_allowlist_by_subagent
+
     modified_disabled_tools = list(disabled_tools) if disabled_tools else []
 
     if "search_knowledge_base" not in modified_disabled_tools:
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 00220d269..14d5d8eb7 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
@@ -9,9 +9,10 @@ matching OpenCode's ``permission/index.ts`` evaluation order):
    needs to *deny* what the user has explicitly forbidden; the default
    ``ask`` fallback would otherwise double-prompt every safe read-only
    call.
-2. ``extra_rulesets`` — caller-supplied rulesets. Each subagent
-   contributes its own (KB: destructive-FS ``ask`` rules; connectors:
-   per-tool ``allow``/``ask``).
+2. ``subagent_rulesets`` — caller-supplied rulesets contributed by the
+   consuming subagent. Each subagent passes its coded rules (KB:
+   destructive-FS ``ask`` rules; connectors: per-tool ``allow``/``ask``)
+   plus, when present, the user's persisted allow-list for that subagent.
 
 Connector deny synthesis from ``new_chat._synthesize_connector_deny_rules``
 is intentionally NOT replicated: the multi-agent orchestrator already
@@ -36,32 +37,34 @@ _SURFSENSE_DEFAULTS = Ruleset(
 def build_permission_mw(
     *,
     flags: AgentFeatureFlags,
-    extra_rulesets: list[Ruleset] | None = None,
+    subagent_rulesets: list[Ruleset] | None = None,
 ) -> PermissionMiddleware | None:
     """Return a configured :class:`PermissionMiddleware` or ``None`` when no work is needed.
 
     Args:
         flags: Feature toggles. ``enable_permission`` switches the engine on;
             ``disable_new_agent_stack`` overrides everything for safety.
-        extra_rulesets: Caller-supplied rulesets layered after the defaults.
-            Subagents pass their own ruleset here so each subagent owns its
-            rules without aliasing a shared engine. Presence of any extra
-            ruleset forces the middleware on regardless of
-            ``enable_permission`` — an explicit ``ask`` rule always asks.
+        subagent_rulesets: Caller-supplied rulesets layered after the
+            defaults. Subagents pass their own coded ruleset here (and,
+            when present, the user's persisted allow-list for that
+            subagent) so each subagent owns its own rule surface without
+            aliasing a shared engine. Presence of any subagent ruleset
+            forces the middleware on regardless of ``enable_permission`` —
+            an explicit ``ask`` rule always asks.
 
     Returns:
         ``None`` when the engine has no rules to enforce
-        (``enable_permission=False`` and no extras); a configured middleware
-        otherwise.
+        (``enable_permission=False`` and no subagent rulesets); a
+        configured middleware otherwise.
     """
     permission_enabled = flags.enable_permission and not flags.disable_new_agent_stack
-    has_extras = bool(extra_rulesets)
-    if not (permission_enabled or has_extras):
+    has_subagent_rulesets = bool(subagent_rulesets)
+    if not (permission_enabled or has_subagent_rulesets):
         return None
 
     rulesets: list[Ruleset] = [_SURFSENSE_DEFAULTS]
-    if extra_rulesets:
-        rulesets.extend(extra_rulesets)
+    if subagent_rulesets:
+        rulesets.extend(subagent_rulesets)
     return PermissionMiddleware(rulesets=rulesets)
 
 
diff --git a/surfsense_backend/app/agents/multi_agent_chat/subagents/builtins/deliverables/agent.py b/surfsense_backend/app/agents/multi_agent_chat/subagents/builtins/deliverables/agent.py
index 9fad9f93b..396e0ec79 100644
--- a/surfsense_backend/app/agents/multi_agent_chat/subagents/builtins/deliverables/agent.py
+++ b/surfsense_backend/app/agents/multi_agent_chat/subagents/builtins/deliverables/agent.py
@@ -38,7 +38,7 @@ def build_subagent(
         system_prompt=system_prompt,
         tools=tools,
         ruleset=RULESET,
-        flags=dependencies["flags"],
+        dependencies=dependencies,
         model=model,
         middleware_stack=middleware_stack,
     )
diff --git a/surfsense_backend/app/agents/multi_agent_chat/subagents/builtins/knowledge_base/agent.py b/surfsense_backend/app/agents/multi_agent_chat/subagents/builtins/knowledge_base/agent.py
index d3ed2885f..c6a0220ec 100644
--- a/surfsense_backend/app/agents/multi_agent_chat/subagents/builtins/knowledge_base/agent.py
+++ b/surfsense_backend/app/agents/multi_agent_chat/subagents/builtins/knowledge_base/agent.py
@@ -55,6 +55,7 @@ def build_subagent(
                 dependencies=dependencies,
                 middleware_stack=middleware_stack,
                 read_only=False,
+                subagent_name=NAME,
                 ruleset=KB_RULESET,
             ),
         },
@@ -83,6 +84,7 @@ def build_readonly_subagent(
                 dependencies=dependencies,
                 middleware_stack=middleware_stack,
                 read_only=True,
+                subagent_name=READONLY_NAME,
                 ruleset=None,
             ),
         },
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 5f4256448..e6c969678 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
@@ -33,20 +33,46 @@ from app.agents.new_chat.filesystem_selection import FilesystemMode
 from app.agents.new_chat.permissions import Ruleset
 
 
+def _kb_user_allowlist(
+    dependencies: dict[str, Any], subagent_name: str
+) -> Ruleset | None:
+    """Return the user's persisted allow-rules for ``subagent_name`` if any.
+
+    KB does not currently expose an "Always Allow" UI surface (the FE
+    button is MCP-only today), but the wiring is symmetrical with the
+    connector subagents so that adding KB trust later is a one-line
+    backend change.
+    """
+    by_subagent = dependencies.get("user_allowlist_by_subagent") or {}
+    user_allowlist = by_subagent.get(subagent_name)
+    if isinstance(user_allowlist, Ruleset) and user_allowlist.rules:
+        return user_allowlist
+    return None
+
+
 def build_kb_middleware(
     *,
     llm: BaseChatModel,
     dependencies: dict[str, Any],
     middleware_stack: dict[str, Any] | None,
     read_only: bool,
+    subagent_name: str,
     ruleset: Ruleset | None = None,
 ) -> list[Any]:
     """Compose the KB subagent's middleware list.
 
-    ``ruleset`` is the KB-owned permission ruleset (typically the
-    destructive-FS ask rules). When provided, a dedicated
-    :class:`PermissionMiddleware` is appended so KB enforces approval at
-    the rule layer.
+    Args:
+        subagent_name: Identity of the subagent being built (e.g.
+            ``"knowledge_base"``, ``"knowledge_base_readonly"``). Used to
+            look up the user's persistent allow-list bucket in
+            ``dependencies["user_allowlist_by_subagent"]``.
+        ruleset: The KB-owned permission ruleset (typically the
+            destructive-FS ``ask`` rules). When provided, a dedicated
+            :class:`PermissionMiddleware` is appended so KB enforces
+            approval at the rule layer. The user's persistent allow-list
+            for ``subagent_name`` is layered after ``ruleset`` so user
+            ``allow`` rules override coded ``ask`` rules via
+            last-match-wins.
     """
     mws = middleware_stack or {}
     filesystem_mode: FilesystemMode = dependencies["filesystem_mode"]
@@ -61,11 +87,13 @@ def build_kb_middleware(
         )
         if m is not None
     ]
-    permission_mw = (
-        build_permission_mw(flags=flags, extra_rulesets=[ruleset])
-        if (ruleset is not None and flags is not None)
-        else None
-    )
+    permission_mw = None
+    if ruleset is not None and flags is not None:
+        rulesets: list[Ruleset] = [ruleset]
+        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)
     return [
         mws["todos"],
         build_kb_context_projection_mw(),
diff --git a/surfsense_backend/app/agents/multi_agent_chat/subagents/builtins/memory/agent.py b/surfsense_backend/app/agents/multi_agent_chat/subagents/builtins/memory/agent.py
index 103bb0cfb..84ab0c2fb 100644
--- a/surfsense_backend/app/agents/multi_agent_chat/subagents/builtins/memory/agent.py
+++ b/surfsense_backend/app/agents/multi_agent_chat/subagents/builtins/memory/agent.py
@@ -33,7 +33,7 @@ def build_subagent(
         system_prompt=system_prompt,
         tools=tools,
         ruleset=RULESET,
-        flags=dependencies["flags"],
+        dependencies=dependencies,
         model=model,
         middleware_stack=middleware_stack,
     )
diff --git a/surfsense_backend/app/agents/multi_agent_chat/subagents/builtins/research/agent.py b/surfsense_backend/app/agents/multi_agent_chat/subagents/builtins/research/agent.py
index 7b37b4228..37026bebd 100644
--- a/surfsense_backend/app/agents/multi_agent_chat/subagents/builtins/research/agent.py
+++ b/surfsense_backend/app/agents/multi_agent_chat/subagents/builtins/research/agent.py
@@ -33,7 +33,7 @@ def build_subagent(
         system_prompt=system_prompt,
         tools=tools,
         ruleset=RULESET,
-        flags=dependencies["flags"],
+        dependencies=dependencies,
         model=model,
         middleware_stack=middleware_stack,
     )
diff --git a/surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/airtable/agent.py b/surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/airtable/agent.py
index 129952dae..d7648d407 100644
--- a/surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/airtable/agent.py
+++ b/surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/airtable/agent.py
@@ -37,7 +37,7 @@ def build_subagent(
         system_prompt=system_prompt,
         tools=list(mcp_tools or []),
         ruleset=RULESET,
-        flags=dependencies["flags"],
+        dependencies=dependencies,
         model=model,
         middleware_stack=middleware_stack,
     )
diff --git a/surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/calendar/agent.py b/surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/calendar/agent.py
index 695013d2a..7ef706c3d 100644
--- a/surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/calendar/agent.py
+++ b/surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/calendar/agent.py
@@ -38,7 +38,7 @@ def build_subagent(
         system_prompt=system_prompt,
         tools=tools,
         ruleset=RULESET,
-        flags=dependencies["flags"],
+        dependencies=dependencies,
         model=model,
         middleware_stack=middleware_stack,
     )
diff --git a/surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/clickup/agent.py b/surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/clickup/agent.py
index 1fec8aa0c..e1308a100 100644
--- a/surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/clickup/agent.py
+++ b/surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/clickup/agent.py
@@ -37,7 +37,7 @@ def build_subagent(
         system_prompt=system_prompt,
         tools=list(mcp_tools or []),
         ruleset=RULESET,
-        flags=dependencies["flags"],
+        dependencies=dependencies,
         model=model,
         middleware_stack=middleware_stack,
     )
diff --git a/surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/confluence/agent.py b/surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/confluence/agent.py
index fab6ecbbe..5e95c876d 100644
--- a/surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/confluence/agent.py
+++ b/surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/confluence/agent.py
@@ -38,7 +38,7 @@ def build_subagent(
         system_prompt=system_prompt,
         tools=tools,
         ruleset=RULESET,
-        flags=dependencies["flags"],
+        dependencies=dependencies,
         model=model,
         middleware_stack=middleware_stack,
     )
diff --git a/surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/discord/agent.py b/surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/discord/agent.py
index 3bac0dc02..567e72973 100644
--- a/surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/discord/agent.py
+++ b/surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/discord/agent.py
@@ -38,7 +38,7 @@ def build_subagent(
         system_prompt=system_prompt,
         tools=tools,
         ruleset=RULESET,
-        flags=dependencies["flags"],
+        dependencies=dependencies,
         model=model,
         middleware_stack=middleware_stack,
     )
diff --git a/surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/dropbox/agent.py b/surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/dropbox/agent.py
index dd5896869..d3ae6dc83 100644
--- a/surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/dropbox/agent.py
+++ b/surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/dropbox/agent.py
@@ -38,7 +38,7 @@ def build_subagent(
         system_prompt=system_prompt,
         tools=tools,
         ruleset=RULESET,
-        flags=dependencies["flags"],
+        dependencies=dependencies,
         model=model,
         middleware_stack=middleware_stack,
     )
diff --git a/surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/gmail/agent.py b/surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/gmail/agent.py
index fd5b64313..082400eb9 100644
--- a/surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/gmail/agent.py
+++ b/surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/gmail/agent.py
@@ -38,7 +38,7 @@ def build_subagent(
         system_prompt=system_prompt,
         tools=tools,
         ruleset=RULESET,
-        flags=dependencies["flags"],
+        dependencies=dependencies,
         model=model,
         middleware_stack=middleware_stack,
     )
diff --git a/surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/google_drive/agent.py b/surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/google_drive/agent.py
index 7acb7431d..fb4a24ddd 100644
--- a/surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/google_drive/agent.py
+++ b/surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/google_drive/agent.py
@@ -38,7 +38,7 @@ def build_subagent(
         system_prompt=system_prompt,
         tools=tools,
         ruleset=RULESET,
-        flags=dependencies["flags"],
+        dependencies=dependencies,
         model=model,
         middleware_stack=middleware_stack,
     )
diff --git a/surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/jira/agent.py b/surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/jira/agent.py
index 0ad47f45d..ff71d4cf7 100644
--- a/surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/jira/agent.py
+++ b/surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/jira/agent.py
@@ -37,7 +37,7 @@ def build_subagent(
         system_prompt=system_prompt,
         tools=list(mcp_tools or []),
         ruleset=RULESET,
-        flags=dependencies["flags"],
+        dependencies=dependencies,
         model=model,
         middleware_stack=middleware_stack,
     )
diff --git a/surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/linear/agent.py b/surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/linear/agent.py
index 0b0580704..d9b282f2b 100644
--- a/surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/linear/agent.py
+++ b/surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/linear/agent.py
@@ -37,7 +37,7 @@ def build_subagent(
         system_prompt=system_prompt,
         tools=list(mcp_tools or []),
         ruleset=RULESET,
-        flags=dependencies["flags"],
+        dependencies=dependencies,
         model=model,
         middleware_stack=middleware_stack,
     )
diff --git a/surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/luma/agent.py b/surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/luma/agent.py
index b1d3ecead..d84efaed8 100644
--- a/surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/luma/agent.py
+++ b/surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/luma/agent.py
@@ -38,7 +38,7 @@ def build_subagent(
         system_prompt=system_prompt,
         tools=tools,
         ruleset=RULESET,
-        flags=dependencies["flags"],
+        dependencies=dependencies,
         model=model,
         middleware_stack=middleware_stack,
     )
diff --git a/surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/notion/agent.py b/surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/notion/agent.py
index 17c8466ab..8de86b2d8 100644
--- a/surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/notion/agent.py
+++ b/surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/notion/agent.py
@@ -38,7 +38,7 @@ def build_subagent(
         system_prompt=system_prompt,
         tools=tools,
         ruleset=RULESET,
-        flags=dependencies["flags"],
+        dependencies=dependencies,
         model=model,
         middleware_stack=middleware_stack,
     )
diff --git a/surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/onedrive/agent.py b/surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/onedrive/agent.py
index 790d1a133..f7634d8ef 100644
--- a/surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/onedrive/agent.py
+++ b/surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/onedrive/agent.py
@@ -38,7 +38,7 @@ def build_subagent(
         system_prompt=system_prompt,
         tools=tools,
         ruleset=RULESET,
-        flags=dependencies["flags"],
+        dependencies=dependencies,
         model=model,
         middleware_stack=middleware_stack,
     )
diff --git a/surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/slack/agent.py b/surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/slack/agent.py
index d2426d92e..e16956b25 100644
--- a/surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/slack/agent.py
+++ b/surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/slack/agent.py
@@ -37,7 +37,7 @@ def build_subagent(
         system_prompt=system_prompt,
         tools=list(mcp_tools or []),
         ruleset=RULESET,
-        flags=dependencies["flags"],
+        dependencies=dependencies,
         model=model,
         middleware_stack=middleware_stack,
     )
diff --git a/surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/teams/agent.py b/surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/teams/agent.py
index 4e39a52f8..ab808b745 100644
--- a/surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/teams/agent.py
+++ b/surfsense_backend/app/agents/multi_agent_chat/subagents/connectors/teams/agent.py
@@ -38,7 +38,7 @@ def build_subagent(
         system_prompt=system_prompt,
         tools=tools,
         ruleset=RULESET,
-        flags=dependencies["flags"],
+        dependencies=dependencies,
         model=model,
         middleware_stack=middleware_stack,
     )
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 76a6f14f3..c61691405 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
@@ -13,10 +13,26 @@ from app.agents.multi_agent_chat.middleware.shared.permissions import (
     build_permission_mw,
 )
 from app.agents.multi_agent_chat.subagents.shared.spec import SurfSenseSubagentSpec
-from app.agents.new_chat.feature_flags import AgentFeatureFlags
 from app.agents.new_chat.permissions import Ruleset
 
 
+def _user_allowlist_for(
+    dependencies: dict[str, Any], subagent_name: str
+) -> Ruleset | None:
+    """Return the user's persisted allow-rules for ``subagent_name`` if any.
+
+    Populated by the agent factory from
+    :func:`app.services.user_tool_allowlist.fetch_user_allowlist_rulesets`.
+    Returning ``None`` is the common case (fresh accounts, non-MCP
+    subagents, or no "Always Allow" interactions yet).
+    """
+    by_subagent = dependencies.get("user_allowlist_by_subagent") or {}
+    user_allowlist = by_subagent.get(subagent_name)
+    if isinstance(user_allowlist, Ruleset) and user_allowlist.rules:
+        return user_allowlist
+    return None
+
+
 def pack_subagent(
     *,
     name: str,
@@ -24,23 +40,43 @@ def pack_subagent(
     system_prompt: str,
     tools: list[BaseTool],
     ruleset: Ruleset,
-    flags: AgentFeatureFlags,
+    dependencies: dict[str, Any],
     model: BaseChatModel | None = None,
     middleware_stack: dict[str, Any] | None = None,
 ) -> SurfSenseSubagentSpec:
     """Pack the route-local pieces into one sub-agent spec + its Ruleset.
 
     Tool gating is uniformly performed by a per-subagent
-    :class:`PermissionMiddleware` built from the subagent's own
-    ``ruleset`` (layered on top of the SurfSense defaults). The shared
-    ``permission`` slot from ``middleware_stack`` is dropped so each
-    subagent owns its own rule surface.
+    :class:`PermissionMiddleware`. Three rule layers are evaluated
+    earliest-to-latest (last match wins):
+
+    1. SurfSense defaults — single ``allow */*`` rule (added by
+       :func:`build_permission_mw`).
+    2. ``ruleset`` — the subagent's coded approval rules (e.g. KB's
+       destructive-FS ``ask`` rules, connector ``ask`` writes).
+    3. The user's persisted allow-list for this subagent — pulled from
+       ``dependencies['user_allowlist_by_subagent'][name]``. User
+       ``allow`` rules layered last override coded ``ask`` rules,
+       implementing the "Always Allow" UX without re-asking on the
+       next turn.
+
+    The shared ``permission`` slot from ``middleware_stack`` is dropped
+    so each subagent owns its own rule surface and cannot accidentally
+    share state with the main agent's permission middleware.
     """
     if not system_prompt.strip():
         msg = f"Subagent {name!r}: system_prompt is empty"
         raise ValueError(msg)
 
-    per_subagent_perm = build_permission_mw(flags=flags, extra_rulesets=[ruleset])
+    flags = dependencies["flags"]
+    user_allowlist = _user_allowlist_for(dependencies, name)
+    subagent_rulesets: list[Ruleset] = [ruleset]
+    if user_allowlist is not None:
+        subagent_rulesets.append(user_allowlist)
+    per_subagent_perm = build_permission_mw(
+        flags=flags, subagent_rulesets=subagent_rulesets
+    )
+
     prepended: list[Any] = []
     for slot, mw in (middleware_stack or {}).items():
         if mw is None:
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 43ca83aff..6f3f34536 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
@@ -1,9 +1,10 @@
 """Regression: subagent-owned rulesets layer cleanly into ``PermissionMiddleware``.
 
 The KB unification swap (legacy ``interrupt_on`` map → KB-owned ``Ruleset``
-threaded through ``build_permission_mw(extra_rulesets=...)``) must produce
-*exactly one* interrupt per destructive FS call, in LC HITL shape, even
-when ``enable_permission`` is False — destructive ops always ask.
+threaded through ``build_permission_mw(subagent_rulesets=...)``) must
+produce *exactly one* interrupt per destructive FS call, in LC HITL
+shape, even when ``enable_permission`` is False — destructive ops always
+ask.
 
 We exercise the production factory and a real ``PermissionMiddleware`` on a
 real ``StateGraph`` so the test catches regressions in factory gating,
@@ -54,7 +55,7 @@ class _State(TypedDict, total=False):
 def _build_graph_with_permission_middleware(
     *,
     flags: AgentFeatureFlags,
-    extra_rulesets: list[Ruleset] | None,
+    subagent_rulesets: list[Ruleset] | None,
     checkpointer: InMemorySaver,
 ):
     """Compile a one-node graph that emits a tool call for ``rm`` and
@@ -64,7 +65,7 @@ def _build_graph_with_permission_middleware(
     ``after_model`` hook intercepts and (if a rule says ``ask``) raises
     a ``GraphInterrupt`` carrying the LC HITL payload.
     """
-    pm = build_permission_mw(flags=flags, extra_rulesets=extra_rulesets)
+    pm = build_permission_mw(flags=flags, subagent_rulesets=subagent_rulesets)
 
     def node(_state: _State) -> dict[str, Any]:
         msg = AIMessage(
@@ -108,10 +109,10 @@ async def test_kb_ruleset_raises_one_lc_hitl_ask_for_rm_even_when_permission_fla
     checkpointer = InMemorySaver()
     graph, pm = _build_graph_with_permission_middleware(
         flags=flags,
-        extra_rulesets=[_kb_style_ruleset()],
+        subagent_rulesets=[_kb_style_ruleset()],
         checkpointer=checkpointer,
     )
-    assert pm is not None, "extras must force the middleware on"
+    assert pm is not None, "subagent rulesets must force the middleware on"
 
     config = {"configurable": {"thread_id": "kb-cloud-rm"}}
     await graph.ainvoke({"messages": [HumanMessage(content="seed")]}, config)
@@ -136,7 +137,7 @@ async def test_kb_ruleset_resume_with_approve_lets_rm_through():
     checkpointer = InMemorySaver()
     graph, _ = _build_graph_with_permission_middleware(
         flags=flags,
-        extra_rulesets=[_kb_style_ruleset()],
+        subagent_rulesets=[_kb_style_ruleset()],
         checkpointer=checkpointer,
     )
     config = {"configurable": {"thread_id": "kb-cloud-rm-approve"}}
@@ -158,12 +159,12 @@ async def test_kb_ruleset_resume_with_approve_lets_rm_through():
 
 
 @pytest.mark.asyncio
-async def test_no_extras_with_permission_off_skips_middleware_entirely():
-    """No extras + permission off → factory returns ``None`` (no engine).
+async def test_no_subagent_rulesets_with_permission_off_skips_middleware_entirely():
+    """No subagent rulesets + permission off → factory returns ``None`` (no engine).
 
     The legacy gating is preserved when no caller asks for rules: nothing
     runs, nothing pauses.
     """
     flags = AgentFeatureFlags(enable_permission=False)
-    pm = build_permission_mw(flags=flags, extra_rulesets=None)
+    pm = build_permission_mw(flags=flags, subagent_rulesets=None)
     assert pm is None
diff --git a/surfsense_backend/tests/unit/agents/multi_agent_chat/subagents/shared/test_subagent_builder.py b/surfsense_backend/tests/unit/agents/multi_agent_chat/subagents/shared/test_subagent_builder.py
index 4dc98665c..062ea92ec 100644
--- a/surfsense_backend/tests/unit/agents/multi_agent_chat/subagents/shared/test_subagent_builder.py
+++ b/surfsense_backend/tests/unit/agents/multi_agent_chat/subagents/shared/test_subagent_builder.py
@@ -19,11 +19,14 @@ from langchain_core.language_models.fake_chat_models import (
 from langchain_core.messages import AIMessage, BaseMessage, HumanMessage
 from langchain_core.outputs import ChatGeneration, ChatResult
 
+from app.agents.multi_agent_chat.middleware.shared.permissions.middleware.core import (
+    PermissionMiddleware,
+)
 from app.agents.multi_agent_chat.subagents.shared.subagent_builder import (
     pack_subagent,
 )
 from app.agents.new_chat.feature_flags import AgentFeatureFlags
-from app.agents.new_chat.permissions import Ruleset
+from app.agents.new_chat.permissions import Rule, Ruleset, evaluate
 
 
 class RateLimitError(Exception):
@@ -81,7 +84,7 @@ async def test_subagent_recovers_when_primary_llm_fails():
         system_prompt="be helpful",
         tools=[],
         ruleset=Ruleset(origin="resilience_test", rules=[]),
-        flags=AgentFeatureFlags(),
+        dependencies={"flags": AgentFeatureFlags()},
         model=primary,
         middleware_stack={"fallback": ModelFallbackMiddleware(fallback)},
     )
@@ -99,3 +102,142 @@ async def test_subagent_recovers_when_primary_llm_fails():
     final = result["messages"][-1]
     assert isinstance(final, AIMessage)
     assert final.content == "recovered via fallback"
+
+
+def _extract_permission_mw(spec) -> PermissionMiddleware:
+    """Find the lone PermissionMiddleware in a subagent's middleware list."""
+    matches = [m for m in spec["middleware"] if isinstance(m, PermissionMiddleware)]
+    assert len(matches) == 1, "expected exactly one PermissionMiddleware"
+    return matches[0]
+
+
+def test_user_allowlist_overrides_coded_ask_via_last_match_wins():
+    """User ``allow`` rules promoted via "Always Allow" must beat coded ``ask`` rules."""
+    coded = Ruleset(
+        origin="connector",
+        rules=[Rule(permission="save_issue", pattern="*", action="ask")],
+    )
+    user_allowlist = Ruleset(
+        origin="user_allowlist:connector",
+        rules=[Rule(permission="save_issue", pattern="*", action="allow")],
+    )
+
+    result = pack_subagent(
+        name="connector",
+        description="test connector",
+        system_prompt="x",
+        tools=[],
+        ruleset=coded,
+        dependencies={
+            "flags": AgentFeatureFlags(),
+            "user_allowlist_by_subagent": {"connector": user_allowlist},
+        },
+    )
+
+    mw = _extract_permission_mw(result.spec)
+    decided = evaluate("save_issue", "*", *mw._static_rulesets)
+    assert decided.action == "allow", (
+        f"user_allowlist must override coded ask; got {decided!r}"
+    )
+
+
+def test_coded_ask_stays_when_user_allowlist_unrelated():
+    """User ``allow`` rules for OTHER tools must not leak into asked-tools."""
+    coded = Ruleset(
+        origin="connector",
+        rules=[Rule(permission="delete_issue", pattern="*", action="ask")],
+    )
+    user_allowlist = Ruleset(
+        origin="user_allowlist:connector",
+        rules=[Rule(permission="save_issue", pattern="*", action="allow")],
+    )
+
+    result = pack_subagent(
+        name="connector",
+        description="test",
+        system_prompt="x",
+        tools=[],
+        ruleset=coded,
+        dependencies={
+            "flags": AgentFeatureFlags(),
+            "user_allowlist_by_subagent": {"connector": user_allowlist},
+        },
+    )
+
+    mw = _extract_permission_mw(result.spec)
+    decided = evaluate("delete_issue", "*", *mw._static_rulesets)
+    assert decided.action == "ask"
+
+
+def test_missing_user_allowlist_keeps_coded_behaviour():
+    """``dependencies`` without ``user_allowlist_by_subagent`` is the common case."""
+    coded = Ruleset(
+        origin="connector",
+        rules=[Rule(permission="save_issue", pattern="*", action="ask")],
+    )
+
+    result = pack_subagent(
+        name="connector",
+        description="test",
+        system_prompt="x",
+        tools=[],
+        ruleset=coded,
+        dependencies={"flags": AgentFeatureFlags()},
+    )
+
+    mw = _extract_permission_mw(result.spec)
+    decided = evaluate("save_issue", "*", *mw._static_rulesets)
+    assert decided.action == "ask"
+
+
+def test_user_allowlist_for_different_subagent_does_not_leak():
+    """User trust for ``linear`` must not affect a ``jira`` subagent compile."""
+    coded = Ruleset(
+        origin="jira",
+        rules=[Rule(permission="save_issue", pattern="*", action="ask")],
+    )
+    linear_allowlist = Ruleset(
+        origin="user_allowlist:linear",
+        rules=[Rule(permission="save_issue", pattern="*", action="allow")],
+    )
+
+    result = pack_subagent(
+        name="jira",
+        description="test",
+        system_prompt="x",
+        tools=[],
+        ruleset=coded,
+        dependencies={
+            "flags": AgentFeatureFlags(),
+            "user_allowlist_by_subagent": {"linear": linear_allowlist},
+        },
+    )
+
+    mw = _extract_permission_mw(result.spec)
+    decided = evaluate("save_issue", "*", *mw._static_rulesets)
+    assert decided.action == "ask"
+
+
+def test_empty_user_allowlist_is_tolerated():
+    """An empty ``Ruleset`` (no rules) must not flip evaluation to allow-everything."""
+    coded = Ruleset(
+        origin="connector",
+        rules=[Rule(permission="save_issue", pattern="*", action="ask")],
+    )
+    empty = Ruleset(origin="user_allowlist:connector", rules=[])
+
+    result = pack_subagent(
+        name="connector",
+        description="test",
+        system_prompt="x",
+        tools=[],
+        ruleset=coded,
+        dependencies={
+            "flags": AgentFeatureFlags(),
+            "user_allowlist_by_subagent": {"connector": empty},
+        },
+    )
+
+    mw = _extract_permission_mw(result.spec)
+    decided = evaluate("save_issue", "*", *mw._static_rulesets)
+    assert decided.action == "ask"