diff --git a/tests/gateway/test_cron_shutdown_drain.py b/tests/gateway/test_cron_shutdown_drain.py
new file mode 100644
index 00000000000..8029c6e70c2
--- /dev/null
+++ b/tests/gateway/test_cron_shutdown_drain.py
@@ -0,0 +1,73 @@
+"""Regression tests for #58818.
+
+On restart the gateway must drain an in-flight cron delivery instead of
+dropping it. A cron delivery is a coroutine scheduled onto the gateway event
+loop (``safe_schedule_threadsafe``) while the ticker thread blocks on its
+future. The shutdown wait therefore must NOT block the loop with a synchronous
+``thread.join()`` — doing so deadlocks the delivery (the loop can never run it)
+and the message is silently lost. ``_await_thread_exit`` waits cooperatively so
+the pending delivery completes first.
+"""
+import asyncio
+import threading
+
+import pytest
+
+import gateway.run as gateway_run
+
+
+@pytest.mark.asyncio
+async def test_await_thread_exit_lets_loop_scheduled_delivery_complete():
+    # Reproduces the drop: the worker schedules a coroutine onto THIS loop and
+    # blocks on its result, exactly like cron/_deliver_result. A blocking join
+    # would deadlock it; the cooperative wait lets it finish.
+    loop = asyncio.get_running_loop()
+    delivered = threading.Event()
+    worker_done = threading.Event()
+
+    async def _delivery():
+        await asyncio.sleep(0.05)
+        delivered.set()
+        return "ok"
+
+    def _cron_worker():
+        fut = asyncio.run_coroutine_threadsafe(_delivery(), loop)
+        fut.result(timeout=10)
+        worker_done.set()
+
+    thread = threading.Thread(target=_cron_worker, daemon=True)
+    thread.start()
+
+    exited = await gateway_run._await_thread_exit(thread, timeout=10)
+
+    assert exited is True
+    assert delivered.is_set(), "in-flight delivery coroutine never ran (loop was blocked)"
+    assert worker_done.is_set()
+
+
+@pytest.mark.asyncio
+async def test_await_thread_exit_returns_false_on_timeout():
+    keep_alive = threading.Event()
+
+    def _spin():
+        keep_alive.wait(5)
+
+    thread = threading.Thread(target=_spin, daemon=True)
+    thread.start()
+    try:
+        exited = await gateway_run._await_thread_exit(thread, timeout=0.2, poll=0.02)
+        assert exited is False
+        assert thread.is_alive()
+    finally:
+        keep_alive.set()
+        thread.join(timeout=2)
+
+
+@pytest.mark.asyncio
+async def test_await_thread_exit_handles_none_and_dead_thread():
+    assert await gateway_run._await_thread_exit(None, timeout=1) is True
+
+    thread = threading.Thread(target=lambda: None, daemon=True)
+    thread.start()
+    thread.join(timeout=2)
+    assert await gateway_run._await_thread_exit(thread, timeout=1) is True