diff --git a/tests/gateway/test_kanban_notifier.py b/tests/gateway/test_kanban_notifier.py
index a7a5fcbb1ee..8e85f045037 100644
--- a/tests/gateway/test_kanban_notifier.py
+++ b/tests/gateway/test_kanban_notifier.py
@@ -172,3 +172,65 @@ def test_kanban_notifier_rewinds_claim_on_send_exception(tmp_path, monkeypatch):
     # still returns the event for retry on the next tick.
     assert adapter.attempts >= 1, "send should have been attempted at least once"
     assert [ev.kind for ev in _unseen_terminal_events(tid)] == ["completed"]
+
+
+def test_notifier_redelivers_same_kind_on_dispatch_cycle(tmp_path, monkeypatch):
+    """A retry cycle (crashed → reclaimed → crashed) notifies the user twice.
+
+    Before #21398 the notifier auto-unsubscribed on any terminal event kind
+    (gave_up / crashed / timed_out), so the second crash in a respawn cycle
+    silently dropped — the subscription was already gone. This test pins the
+    new contract: subscription survives non-final terminal events; the
+    cursor handles dedup.
+
+    Two crashes ten seconds apart on the same task — both should land on
+    the adapter.
+    """
+    db_path = tmp_path / "redeliver-cycle.db"
+    monkeypatch.setenv("HERMES_KANBAN_DB", str(db_path))
+    kb.init_db()
+
+    conn = kb.connect()
+    try:
+        tid = kb.create_task(conn, title="cycle test", assignee="worker")
+        kb.add_notify_sub(conn, task_id=tid, platform="telegram", chat_id="chat-1")
+        # First crash — fired by the dispatcher when the worker PID dies.
+        kb._append_event(conn, tid, kind="crashed")
+    finally:
+        conn.close()
+
+    adapter = RecordingAdapter()
+    runner = _make_runner(adapter)
+    asyncio.run(_run_one_notifier_tick(monkeypatch, runner))
+
+    # First crash delivered.
+    assert len(adapter.sent) == 1
+    assert "crashed" in adapter.sent[0]["text"].lower()
+
+    # Subscription survives — the cursor advanced past event #1, but the
+    # row is still there.
+    conn = kb.connect()
+    try:
+        subs = kb.list_notify_subs(conn, tid)
+        assert len(subs) == 1, (
+            "Subscription must survive a crashed event so a respawn-cycle "
+            "second crash also notifies the user (issue #21398)."
+        )
+
+        # Second crash — same task, same dispatcher (or a respawn). Append
+        # another event to simulate the dispatcher firing crashed a second
+        # time during retry.
+        kb._append_event(conn, tid, kind="crashed")
+    finally:
+        conn.close()
+
+    # New tick: the second event has a fresh id past the cursor advance,
+    # so it gets claimed and delivered.
+    runner = _make_runner(adapter)
+    asyncio.run(_run_one_notifier_tick(monkeypatch, runner))
+
+    assert len(adapter.sent) == 2, (
+        f"Second crashed event should also notify; got {len(adapter.sent)} "
+        f"deliveries (texts: {[d['text'] for d in adapter.sent]})"
+    )
+    assert "crashed" in adapter.sent[1]["text"].lower()
diff --git a/tests/hermes_cli/test_kanban_notify.py b/tests/hermes_cli/test_kanban_notify.py
index 3b8cf4865d9..6e59fb45aa7 100644
--- a/tests/hermes_cli/test_kanban_notify.py
+++ b/tests/hermes_cli/test_kanban_notify.py
@@ -76,7 +76,13 @@ async def test_notifier_unsubs_after_completed_event(kanban_home):
 @pytest.mark.parametrize('kind', ["gave_up", "crashed", "timed_out"])
 async def test_notifier_unsubs_after_abnormal_events(kind, kanban_home):
     """
-    Event kind of gave_up, crashed, time_out would be cover, and remove subscription
+    Event kinds gave_up / crashed / timed_out send a notification but DO
+    NOT delete the subscription. The dispatcher may respawn the task and
+    fire the same event kind again (e.g. a worker that crashes, gets
+    reclaimed, and crashes a second time); the user must hear about the
+    second event too. Subscriptions are removed only when the task hits
+    a truly final status (done / archived) — see the comment on
+    TERMINAL_KINDS in gateway/run.py and PR #21398.
     """
     import hermes_cli.kanban_db as kb
     from gateway.run import GatewayRunner
@@ -114,15 +120,27 @@ async def test_notifier_unsubs_after_abnormal_events(kind, kanban_home):
             timeout=10.0,
         )
 
+    # The user is notified about the abnormal event...
     fake_adapter.send.assert_called_once()
     assert kind.replace('_', ' ') in fake_adapter.send.call_args[0][1]
 
+    # ...but the subscription survives so a respawn-then-same-event cycle
+    # reaches the user too. The cursor (last_event_id) advanced inside
+    # the same write txn as the claim, so the same event won't re-fire.
     conn = kb.connect()
     try:
         subs = kb.list_notify_subs(conn, tid)
     finally:
         conn.close()
-    assert subs == [], "Subscription should be unsub after abnormal crash"
+    assert len(subs) == 1, (
+        f"Subscription should survive {kind!r} so the next cycle of the "
+        f"same event reaches the user; got {subs!r}"
+    )
+    assert int(subs[0]["last_event_id"]) >= 1, (
+        "Cursor should have advanced past the delivered event "
+        "(claim_unseen_events_for_sub advances atomically inside the "
+        "same write txn as the read)."
+    )
 
 
 @pytest.mark.asyncio