diff --git a/tests/gateway/test_update_cron_drain.py b/tests/gateway/test_update_cron_drain.py
new file mode 100644
index 00000000000..ee34d72cd82
--- /dev/null
+++ b/tests/gateway/test_update_cron_drain.py
@@ -0,0 +1,86 @@
+"""Regression tests for #60432.
+
+``/update`` (and other gateway shutdown paths) must drain in-flight cron jobs
+before ``process_registry.kill_all()`` runs in final-cleanup.  Cron work runs on
+a thread-pool worker and is tracked in ``cron.scheduler._running_job_ids``, not
+in ``GatewayRunner._running_agents`` — so a zero-agent drain must still wait
+for cron to finish (or time out and take the interrupt/kill path).
+"""
+import asyncio
+from unittest.mock import AsyncMock, MagicMock, patch
+
+import pytest
+
+from tests.gateway.restart_test_helpers import make_restart_runner
+
+
+@pytest.mark.asyncio
+async def test_drain_active_agents_waits_for_in_flight_cron_jobs():
+    runner, _adapter = make_restart_runner()
+    runner._running_agents = {}
+
+    cron_count = [1]
+
+    def _cron_in_flight():
+        return cron_count[0]
+
+    async def finish_cron():
+        await asyncio.sleep(0.15)
+        cron_count[0] = 0
+
+    with patch("cron.scheduler.cron_jobs_in_flight", side_effect=_cron_in_flight):
+        task = asyncio.create_task(finish_cron())
+        _snapshot, timed_out = await runner._drain_active_agents(1.0)
+        await task
+
+    assert timed_out is False
+    assert _snapshot == {}
+
+
+@pytest.mark.asyncio
+async def test_drain_active_agents_times_out_when_cron_still_running():
+    runner, _adapter = make_restart_runner()
+    runner._running_agents = {}
+
+    with patch("cron.scheduler.cron_jobs_in_flight", return_value=1):
+        _snapshot, timed_out = await runner._drain_active_agents(0.05)
+
+    assert timed_out is True
+    assert _snapshot == {}
+
+
+@pytest.mark.asyncio
+async def test_gateway_stop_waits_for_cron_before_final_tool_kill():
+    """Graceful cron completion must finish before final-cleanup kill_all."""
+    runner, adapter = make_restart_runner()
+    runner._restart_drain_timeout = 1.0
+
+    cron_count = [1]
+    call_order: list[str] = []
+
+    def _cron_in_flight():
+        return cron_count[0]
+
+    def _fake_kill_all(task_id=None):
+        call_order.append("kill_all")
+        return 0
+
+    async def finish_cron():
+        await asyncio.sleep(0.12)
+        cron_count[0] = 0
+
+    with (
+        patch("cron.scheduler.cron_jobs_in_flight", side_effect=_cron_in_flight),
+        patch("gateway.status.remove_pid_file"),
+        patch("gateway.status.write_runtime_status"),
+        patch("agent.auxiliary_client.shutdown_cached_clients"),
+        patch("tools.process_registry.process_registry") as registry_mock,
+    ):
+        registry_mock.kill_all.side_effect = _fake_kill_all
+        adapter.disconnect = AsyncMock()
+
+        cron_task = asyncio.create_task(finish_cron())
+        await runner.stop()
+        await cron_task
+
+    assert call_order == ["kill_all"]