diff --git a/tests/gateway/test_approve_deny_commands.py b/tests/gateway/test_approve_deny_commands.py
index b1c192f1ac..ebe4d59172 100644
--- a/tests/gateway/test_approve_deny_commands.py
+++ b/tests/gateway/test_approve_deny_commands.py
@@ -173,6 +173,23 @@ class TestBlockingGatewayApproval:
         assert e1.event.is_set()
         assert e2.event.is_set()
 
+    def test_clear_session_denies_and_signals_all_entries(self):
+        """clear_session must wake blocked entries during boundary cleanup."""
+        from tools.approval import clear_session, _ApprovalEntry, _gateway_queues
+
+        session_key = "test-boundary-cleanup"
+        e1 = _ApprovalEntry({"command": "cmd1"})
+        e2 = _ApprovalEntry({"command": "cmd2"})
+        _gateway_queues[session_key] = [e1, e2]
+
+        clear_session(session_key)
+
+        assert e1.event.is_set()
+        assert e2.event.is_set()
+        assert e1.result == "deny"
+        assert e2.result == "deny"
+        assert session_key not in _gateway_queues
+
 
 # ------------------------------------------------------------------
 # /approve command
diff --git a/tests/gateway/test_session_boundary_security_state.py b/tests/gateway/test_session_boundary_security_state.py
index f7f4124951..00c1568de1 100644
--- a/tests/gateway/test_session_boundary_security_state.py
+++ b/tests/gateway/test_session_boundary_security_state.py
@@ -10,6 +10,7 @@ from gateway.platforms.base import MessageEvent
 from gateway.session import SessionEntry, SessionSource, build_session_key
 from tools import approval as approval_mod
 from tools.approval import (
+    _ApprovalEntry,
     approve_session,
     enable_session_yolo,
     is_approved,
@@ -214,3 +215,30 @@ def test_clear_session_boundary_security_state_is_scoped():
     runner._clear_session_boundary_security_state("")
     assert is_approved(other_key, "recursive delete") is True
     assert other_key in runner._update_prompt_pending
+
+
+def test_clear_session_boundary_security_state_wakes_blocked_approvals():
+    """Boundary cleanup must cancel blocked approval waiters immediately."""
+    from gateway.run import GatewayRunner
+
+    runner = object.__new__(GatewayRunner)
+    runner._pending_approvals = {}
+    runner._update_prompt_pending = {}
+
+    source = _make_source()
+    session_key = build_session_key(source)
+    other_key = "agent:main:telegram:dm:other-chat"
+
+    target_entry = _ApprovalEntry({"command": "rm -rf /tmp/demo"})
+    other_entry = _ApprovalEntry({"command": "rm -rf /tmp/other"})
+    approval_mod._gateway_queues[session_key] = [target_entry]
+    approval_mod._gateway_queues[other_key] = [other_entry]
+
+    runner._clear_session_boundary_security_state(session_key)
+
+    assert target_entry.event.is_set()
+    assert target_entry.result == "deny"
+    assert other_entry.event.is_set() is False
+    assert other_entry.result is None
+    assert session_key not in approval_mod._gateway_queues
+    assert other_key in approval_mod._gateway_queues
diff --git a/tools/approval.py b/tools/approval.py
index 78fb481783..aa20a86aec 100644
--- a/tools/approval.py
+++ b/tools/approval.py
@@ -400,8 +400,8 @@ def unregister_gateway_notify(session_key: str) -> None:
     with _lock:
         _gateway_notify_cbs.pop(session_key, None)
         entries = _gateway_queues.pop(session_key, [])
-        for entry in entries:
-            entry.event.set()
+    for entry in entries:
+        entry.event.set()
 
 
 def resolve_gateway_approval(session_key: str, choice: str,
@@ -475,7 +475,12 @@ def clear_session(session_key: str) -> None:
         _session_approved.pop(session_key, None)
         _session_yolo.discard(session_key)
         _pending.pop(session_key, None)
-        _gateway_queues.pop(session_key, None)
+        entries = _gateway_queues.pop(session_key, [])
+    for entry in entries:
+        # Session-boundary cleanup should cancel any blocked approval waits
+        # immediately so the old run can unwind instead of idling until timeout.
+        entry.result = "deny"
+        entry.event.set()
 
 
 def is_session_yolo_enabled(session_key: str) -> bool: