diff --git a/tests/tools/test_request_tool_approval.py b/tests/tools/test_request_tool_approval.py
index 29fd459bcb..d1a390a45a 100644
--- a/tests/tools/test_request_tool_approval.py
+++ b/tests/tools/test_request_tool_approval.py
@@ -168,6 +168,54 @@ class TestRequestToolApproval:
         assert res["approved"] is False
         assert "no interactive user or gateway" in res["message"].lower()
 
+    def test_api_server_exec_ask_uses_approval_bridge(self, monkeypatch):
+        """Plugin escalation reaches the /v1/runs approval bridge when ask mode is active."""
+        monkeypatch.setattr(approval, "_is_interactive_cli", lambda: False)
+        monkeypatch.setattr(approval, "_is_gateway_approval_context", lambda: False)
+        monkeypatch.setattr(tools_approval_context, "_is_gateway_approval_context", lambda: False)
+        monkeypatch.setattr(approval, "_is_cron_approval_context", lambda: False)
+        monkeypatch.setattr(tools_approval_context, "_is_cron_approval_context", lambda: False)
+        monkeypatch.setattr(approval, "_is_single_query_approval_context", lambda: False)
+        monkeypatch.setattr(approval_context, "_get_approval_mode", lambda: "manual")
+        monkeypatch.setenv("HERMES_EXEC_ASK", "1")
+        monkeypatch.setenv("HERMES_SESSION_PLATFORM", "api_server")
+
+        notified = []
+
+        def approve(data):
+            notified.append(data)
+            assert approval.resolve_gateway_approval(
+                "test-session", "once", request_id=data["request_id"]
+            ) == 1
+
+        approval.register_gateway_notify("test-session", approve)
+        try:
+            res = request_tool_approval("home_lock", "unlock the front door", rule_key="unlock")
+        finally:
+            approval.unregister_gateway_notify("test-session")
+
+        assert res["approved"] is True
+        assert len(notified) == 1
+        assert notified[0]["pattern_key"] == "plugin_rule:unlock"
+
+    def test_api_server_without_exec_ask_remains_fail_closed(self, monkeypatch):
+        """An api_server call without an active approval bridge must not run ungated."""
+        monkeypatch.setattr(approval, "_is_interactive_cli", lambda: False)
+        monkeypatch.setattr(approval, "_is_gateway_approval_context", lambda: False)
+        monkeypatch.setattr(tools_approval_context, "_is_gateway_approval_context", lambda: False)
+        monkeypatch.setattr(approval, "_is_cron_approval_context", lambda: False)
+        monkeypatch.setattr(tools_approval_context, "_is_cron_approval_context", lambda: False)
+        monkeypatch.setattr(approval, "_is_single_query_approval_context", lambda: False)
+        monkeypatch.setattr(approval_context, "_get_approval_mode", lambda: "manual")
+        monkeypatch.setattr(approval_context, "_get_unattended_approval_mode", lambda: "deny")
+        monkeypatch.delenv("HERMES_EXEC_ASK", raising=False)
+        monkeypatch.setenv("HERMES_SESSION_PLATFORM", "api_server")
+
+        res = request_tool_approval("home_lock", "unlock the front door", rule_key="unlock")
+
+        assert res["approved"] is False
+        assert "unattended platform" in res["message"].lower()
+
     def test_yolo_session_bypasses_gate(self, monkeypatch):
         """A --yolo session skips the plugin approval gate (parity with the
         dangerous-command path, via the shared _run_approval_gate)."""
diff --git a/tools/approval.py b/tools/approval.py
index 984470a7bd..627c7c92c2 100644
--- a/tools/approval.py
+++ b/tools/approval.py
@@ -961,7 +961,8 @@ def _run_approval_gate(
     Order: yolo bypass → session-cache short-circuit → interactive/gateway/unattended branch →
     prompt → persistence. Input-shape checks (hardline, allowlist, pattern detection) are the
     caller's job. ``fail_closed_when_no_human``: a non-interactive, non-gateway, non-cron
-    context BLOCKS instead of auto-approving, so a plugin-flagged action never runs ungated.
+    context without an ask bridge BLOCKS instead of auto-approving, so a plugin-flagged action
+    never runs ungated.
     Unattended deny text is ``ctx.block_message(subject, noun, advice)`` unless the caller passes
     an explicit ``*_deny_message`` (the file-tool write gates word their own).
     """
@@ -976,7 +977,7 @@ def _run_approval_gate(
         return _approved()
 
     approval_callback, is_cli, is_gateway, is_ask = _presence(approval_callback)
-    if not is_cli and not is_gateway:
+    if not is_cli and not is_gateway and not is_ask:
         log_args = (autoapprove_log_prefix, pattern_key, description)
         # Every unattended context resolves instantly — never a pending approval nobody can answer.
         deny_messages = {
@@ -1098,9 +1099,9 @@ def request_tool_approval(tool_name: str, reason: str, *, rule_key: str = "", ap
     it asks the SAME human gate as Tier-2 dangerous shell patterns (session/permanent
     allowlist, CLI prompt, gateway pending, once/session/always/deny, timeout fail-closed), so
     the LLM cannot skip it. Cron honors ``approvals.cron_mode``; any OTHER non-interactive
-    non-gateway context fails CLOSED. ``rule_key`` controls the ``[a]lways`` allowlist grain;
-    when empty it is ``tool_name`` + a hash of ``reason`` so DISTINCT reasons on the same tool
-    persist independently. Returns the ``check_dangerous_command`` result shape.
+    context without an approval bridge fails CLOSED. ``rule_key`` controls the ``[a]lways``
+    allowlist grain; when empty it is ``tool_name`` + a hash of ``reason`` so DISTINCT reasons
+    on the same tool persist independently. Returns the ``check_dangerous_command`` result shape.
     """
     description = reason or f"Plugin requires approval for {tool_name}"
     if not rule_key: