diff --git a/tests/tools/test_approval.py b/tests/tools/test_approval.py
index 3500ede939..1b2f395c74 100644
--- a/tests/tools/test_approval.py
+++ b/tests/tools/test_approval.py
@@ -1016,14 +1016,17 @@ class TestWebhookApprovalExclusion:
 class TestUnattendedPlatformExecAskLeak:
     """A gateway process sets HERMES_EXEC_ASK=1 for EVERY session it serves, so an
     api_server/webhook turn reads as "ask" in ``_presence()`` even though the platform was
-    already excluded from gateway approval contexts. Without a registered notify callback
-    (non-streaming /v1/chat/completions, webhook, msgraph_webhook) the ask branch parks the
-    approval as ``pending_approval`` that no client on that endpoint can ever answer, and
-    ``approvals.unattended_mode`` never runs — the unanswerable stall of #100532.
+    already excluded from gateway approval contexts. Without a surface that can answer the
+    card — non-streaming /v1/chat/completions registers no notify callback, and
+    webhook/msgraph_webhook register one on every turn yet render no approval surface and
+    have no reader — the ask branch blocks for the full approval timeout with no human who
+    can resolve it, and ``approvals.unattended_mode`` never runs (#100532).
 
-    Fix: ``_presence()`` drops ``is_ask`` for unattended-platform sessions without a notify
-    callback, so the unattended branch resolves instantly from ``approvals.unattended_mode``.
-    ``/v1/runs`` and streaming chat completions register a callback and keep the ask path.
+    Fix: ``_presence()`` drops ``is_ask`` for unattended-platform sessions that no client can
+    answer — no notify callback on api_server, or a notifier-blind platform (webhook,
+    msgraph_webhook) where the TurnRunner lane registers one unconditionally — so the
+    unattended branch resolves instantly from ``approvals.unattended_mode``. ``/v1/runs`` and
+    streaming chat completions register a callback and keep the ask path.
     """
 
     def _isolate(self, monkeypatch, *, platform="api_server"):
@@ -1100,6 +1103,48 @@ class TestUnattendedPlatformExecAskLeak:
         _, _is_cli, _is_gateway, is_ask = approval_mod._presence()
         assert is_ask is True
 
+    def test_webhook_registered_notifier_still_resolves_unattended(self, monkeypatch):
+        """webhook/msgraph_webhook residual of #100532: the generic TurnRunner lane registers a
+        notify callback for *every* inbound turn (``_run_conversation_with_approval`` registers
+        unconditionally), yet the WebhookAdapter renders no ``send_exec_approval``/``/approve``
+        surface and the inbound lane is ``POST -> 202`` with no reader — so a registered
+        notifier there does not mean anyone can answer. The ask leak must resolve from
+        ``approvals.unattended_mode`` instead of blocking the full approval timeout."""
+        import tools.approval as approval_mod
+        from tools.approval import check_all_command_guards
+
+        self._isolate(monkeypatch, platform="webhook")
+        monkeypatch.setattr(approval_mod, "_smart_verdict",
+                            lambda *a, **k: pytest.fail("guardian ran after unattended resolution"))
+
+        def _no_human(data):
+            pytest.fail("approval card delivered to a platform with no approval transport")
+
+        approval_mod.register_gateway_notify("test-unattended-ask-leak", _no_human)
+        try:
+            result = check_all_command_guards("pkill -9 -f soffice", "local")
+        finally:
+            approval_mod.unregister_gateway_notify("test-unattended-ask-leak")
+
+        assert result["approved"] is False
+        assert result.get("status") != "pending_approval"
+        assert result.get("approval_pending") is not True
+        assert "unattended platform" in result["message"]
+        assert "approvals.unattended_mode" in result["message"]
+
+    def test_msgraph_webhook_registered_notifier_drops_ask(self, monkeypatch):
+        """Same shape at the ``_presence()`` level for msgraph_webhook: the TurnRunner-registered
+        notifier must not keep the ask branch alive on a notifier-blind platform."""
+        import tools.approval as approval_mod
+
+        self._isolate(monkeypatch, platform="msgraph_webhook")
+        approval_mod.register_gateway_notify("test-unattended-ask-leak", lambda data: None)
+        try:
+            _, _is_cli, _is_gateway, is_ask = approval_mod._presence()
+            assert is_ask is False
+        finally:
+            approval_mod.unregister_gateway_notify("test-unattended-ask-leak")
+
 
 class TestNormalizationBypass:
     """Obfuscation techniques must not bypass dangerous command detection."""
diff --git a/tools/approval.py b/tools/approval.py
index 8df609aa3a..f3400a8a9a 100644
--- a/tools/approval.py
+++ b/tools/approval.py
@@ -914,23 +914,30 @@ def _presence(approval_callback=None) -> tuple:
     HERMES_INTERACTIVE=1 for sudo prompts, and a gateway sets HERMES_EXEC_ASK=1 at startup and
     passes its environ to every external cron worker (#110932) — in neither can a human answer
     the card, so the gate must resolve from ``approvals.<ctx>_mode`` instead of parking on a
-    pending approval. Unattended *platforms* keep ``is_ask`` only while the session has a
-    registered approval notifier: ``/v1/runs`` and streaming chat completions bridge one
-    (``approval.request`` → ``POST /v1/runs/{id}/approval``). Without a notifier no client on
-    the platform can ever answer, so ``is_ask`` drops too and the unattended branch resolves
-    from ``approvals.unattended_mode`` instead of parking an unanswerable card (#100532)."""
+    pending approval. Unattended *platforms* keep ``is_ask`` only while a client on the session
+    could actually answer: ``/v1/runs`` and streaming chat completions bridge an approval
+    notifier (``approval.request`` → ``POST /v1/runs/{id}/approval``), so on api_server a
+    registered notifier is the discriminator. webhook/msgraph_webhook turns run through the
+    generic TurnRunner lane, which registers a notifier for *every* turn — but those adapters
+    render no approval surface and the inbound lane has no reader, so there ``is_ask`` drops
+    regardless and the unattended branch resolves from ``approvals.unattended_mode`` instead of
+    parking an unanswerable card (#100532)."""
     approval_callback = _resolve_cli_approval_callback(approval_callback)
     is_cli, is_gateway = _is_interactive_cli(), _is_gateway_approval_context()
     is_ask = env_var_enabled("HERMES_EXEC_ASK")
     if _is_single_query_approval_context() or _is_cron_approval_context():
         is_cli = is_gateway = is_ask = False
     elif is_ask and _is_unattended_platform_approval_context() \
-            and _gateway_notify_cb(get_current_session_key()) is None:
+            and (_gateway_notify_cb(get_current_session_key()) is None
+                 or _get_session_platform() in approval_context._NOTIFIER_BLIND_APPROVAL_PLATFORMS):
         # start_gateway() sets HERMES_EXEC_ASK process-wide, so an api_server/webhook turn
         # inside that gateway still reads as "ask" here even though _is_gateway_approval_context()
         # already excluded the platform. /v1/runs and streaming chat register their notify
         # callback before the turn runs; a session with none has no surface that can resolve an
-        # approval — resolve from approvals.unattended_mode, never a pending no one can answer.
+        # approval. webhook/msgraph_webhook are notifier-blind: the generic TurnRunner lane
+        # registers one for every turn while the adapter has no ``send_exec_approval`` and the
+        # POST -> 202 lane has no reader, so a registered callback there answers nothing either
+        # — resolve from approvals.unattended_mode, never a pending no one can answer.
         is_ask = False
     return approval_callback, is_cli, is_gateway, is_ask
 
diff --git a/tools/approval_context.py b/tools/approval_context.py
index a2b60094f0..b28b820c9a 100644
--- a/tools/approval_context.py
+++ b/tools/approval_context.py
@@ -146,6 +146,15 @@ def _is_unattended_platform_approval_context() -> bool:
     return _get_session_platform() in _UNATTENDED_APPROVAL_PLATFORMS
 
 
+# Platforms where a *registered* gateway notify callback still does not mean a human can answer:
+# the generic TurnRunner lane registers one for every inbound turn
+# (``_run_conversation_with_approval`` registers unconditionally, no platform branch), while the
+# adapter renders no ``send_exec_approval``/``/approve`` surface and the inbound lane is a
+# fire-and-forget ``POST -> 202`` with no reader. Notifier presence is only a meaningful
+# "someone can answer" discriminator on api_server, whose turn paths choose whether to register one.
+_NOTIFIER_BLIND_APPROVAL_PLATFORMS = frozenset({"webhook", "msgraph_webhook"})
+
+
 def _is_single_query_approval_context() -> bool:
     """True for a single-query (-q) session: ``hermes chat -q`` exports
     ``HERMES_INTERACTIVE=1`` (so sudo password prompts work) but nobody is waiting