diff --git a/gateway/run.py b/gateway/run.py
index 8683c5a75..af3946d4a 100644
--- a/gateway/run.py
+++ b/gateway/run.py
@@ -2383,10 +2383,23 @@ class GatewayRunner:
                 # existing ``.restart_failure_counts`` stuck-loop counter
                 # (incremented below, threshold 3), which sets
                 # ``suspended=True`` and overrides resume_pending.
+                #
+                # Iterate self._running_agents (current) rather than the
+                # drain-start ``active_agents`` snapshot — the snapshot
+                # may include sessions that finished gracefully during
+                # the drain window, and marking those falsely would give
+                # them a stray restart-interruption system note on their
+                # next turn even though their previous turn completed
+                # cleanly.  Skip pending sentinels for the same reason
+                # _interrupt_running_agents() does: their agent hasn't
+                # started yet, there's nothing to interrupt, and the
+                # session shouldn't carry a misleading resume flag.
                 _resume_reason = (
                     "restart_timeout" if self._restart_requested else "shutdown_timeout"
                 )
-                for _sk in list(active_agents.keys()):
+                for _sk, _agent in list(self._running_agents.items()):
+                    if _agent is _AGENT_PENDING_SENTINEL:
+                        continue
                     try:
                         self.session_store.mark_resume_pending(_sk, _resume_reason)
                     except Exception as _e:
diff --git a/tests/gateway/test_restart_resume_pending.py b/tests/gateway/test_restart_resume_pending.py
index a18d85cc4..c11b2740d 100644
--- a/tests/gateway/test_restart_resume_pending.py
+++ b/tests/gateway/test_restart_resume_pending.py
@@ -516,6 +516,84 @@ async def test_clean_drain_does_not_mark_resume_pending():
     running_agent.interrupt.assert_not_called()
 
 
+@pytest.mark.asyncio
+async def test_drain_timeout_only_marks_still_running_sessions():
+    """A session that finished gracefully during the drain window must
+    NOT be marked ``resume_pending`` — it completed cleanly and its
+    next turn should be a normal fresh turn, not one prefixed with the
+    restart-interruption system note.
+
+    Regression guard for using ``self._running_agents`` at timeout
+    rather than the ``active_agents`` drain-start snapshot.
+    """
+    runner, adapter = make_restart_runner()
+    adapter.disconnect = AsyncMock()
+    # Long enough for the finisher to exit, short enough to still time out
+    # with the stuck session still present.
+    runner._restart_drain_timeout = 0.3
+
+    session_key_finisher = "agent:main:telegram:dm:A"
+    session_key_stuck = "agent:main:telegram:dm:B"
+    runner._running_agents = {
+        session_key_finisher: MagicMock(),
+        session_key_stuck: MagicMock(),
+    }
+
+    async def finish_one():
+        await asyncio.sleep(0.05)
+        runner._running_agents.pop(session_key_finisher, None)
+
+    asyncio.create_task(finish_one())
+
+    session_store = MagicMock()
+    session_store.mark_resume_pending = MagicMock(return_value=True)
+    runner.session_store = session_store
+
+    with patch("gateway.status.remove_pid_file"), patch(
+        "gateway.status.write_runtime_status"
+    ):
+        await runner.stop()
+
+    calls = session_store.mark_resume_pending.call_args_list
+    marked = {args[0][0] for args in calls}
+    # Only the session still running at timeout is marked; the finisher is not.
+    assert marked == {session_key_stuck}
+
+
+@pytest.mark.asyncio
+async def test_drain_timeout_skips_pending_sentinel_sessions():
+    """Pending sentinels — sessions whose AIAgent construction hasn't
+    produced a real agent yet — are skipped by
+    ``_interrupt_running_agents()``.  The resume_pending marking must
+    mirror that: no agent started means no turn was interrupted.
+    """
+    from gateway.run import _AGENT_PENDING_SENTINEL
+
+    runner, adapter = make_restart_runner()
+    adapter.disconnect = AsyncMock()
+    runner._restart_drain_timeout = 0.05
+
+    session_key_real = "agent:main:telegram:dm:A"
+    session_key_sentinel = "agent:main:telegram:dm:B"
+    runner._running_agents = {
+        session_key_real: MagicMock(),
+        session_key_sentinel: _AGENT_PENDING_SENTINEL,
+    }
+
+    session_store = MagicMock()
+    session_store.mark_resume_pending = MagicMock(return_value=True)
+    runner.session_store = session_store
+
+    with patch("gateway.status.remove_pid_file"), patch(
+        "gateway.status.write_runtime_status"
+    ):
+        await runner.stop()
+
+    calls = session_store.mark_resume_pending.call_args_list
+    marked = {args[0][0] for args in calls}
+    assert marked == {session_key_real}
+
+
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