diff --git a/roboco/services/messaging.py b/roboco/services/messaging.py
index 647ec813..97c84248 100644
--- a/roboco/services/messaging.py
+++ b/roboco/services/messaging.py
@@ -536,6 +536,37 @@ class MessagingService(BaseService):
         )
         return result.scalar_one_or_none()
 
+    async def _session_still_timed_out(
+        self,
+        session_id: UUID,
+        *,
+        timeout_seconds: int,
+        max_time_window: timedelta | None,
+    ) -> bool:
+        """Re-check the timeout against a FRESH ``last_activity_at`` from the DB.
+
+        Closes the sweeper TOCTOU: a message may have refreshed
+        ``last_activity_at`` between the candidate SELECT and the close, so the
+        stale in-memory value would close a just-used session. Returns False if
+        the session is no longer timed out / window-exceeded per the fresh row
+        (or was closed concurrently).
+        """
+        now = datetime.now(UTC)
+        result = await self.session.execute(
+            select(
+                SessionTable.last_activity_at,
+                SessionTable.started_at,
+                SessionTable.status,
+            ).where(SessionTable.id == session_id)
+        )
+        row = result.one_or_none()
+        if row is None or row.status != SessionStatus.ACTIVE:
+            return False
+        last = row.last_activity_at or row.started_at
+        if (now - last).total_seconds() >= timeout_seconds:
+            return True
+        return max_time_window is not None and (now - row.started_at) >= max_time_window
+
     async def sweep_timed_out_sessions(self) -> int:
         """Close sessions whose inactivity exceeds `timeout_seconds`.
 
@@ -567,6 +598,16 @@ class MessagingService(BaseService):
             if not (timeout_exceeded or window_exceeded):
                 continue
 
+            # TOCTOU re-check: a message may have refreshed last_activity_at
+            # between the candidate SELECT above and here. Re-read fresh and
+            # skip if the session is no longer timed out (was just used).
+            if not await self._session_still_timed_out(
+                cast("UUID", session.id),
+                timeout_seconds=session.timeout_seconds,
+                max_time_window=session.max_time_window,
+            ):
+                continue
+
             reason = "Inactivity timeout" if timeout_exceeded else "Max time window"
             await self.close_session(cast("UUID", session.id), reason)
             closed += 1
diff --git a/tests/integration/test_messaging_service.py b/tests/integration/test_messaging_service.py
index 00c09fe9..dcc00a7d 100644
--- a/tests/integration/test_messaging_service.py
+++ b/tests/integration/test_messaging_service.py
@@ -1020,6 +1020,38 @@ async def test_sweep_timed_out_sessions_closes_idle_session(
     assert closed >= 1
 
 
+@pytest.mark.asyncio
+async def test_sweep_skips_session_refreshed_after_candidate_select(
+    msg_setup: dict, db_session: AsyncSession
+) -> None:
+    """TOCTOU: a session stale at the candidate SELECT but refreshed (a message
+    landed) before the close must NOT be closed. The sweeper re-reads
+    last_activity_at fresh and skips a just-used session."""
+    svc = msg_setup["svc"]
+    ch = await svc.create_channel(_channel_req(uuid4().hex[:6]))
+    grp = await svc.create_group(GroupCreateRequest(name="g1", channel_id=ch.id))
+    sess = await svc.create_session(
+        SessionCreateRequest(group_id=grp.id, timeout_seconds=1)
+    )
+    sid = sess.id
+    # Stale at SELECT time -> candidate.
+    sess.last_activity_at = datetime.now(UTC) - timedelta(seconds=120)
+    await db_session.flush()
+    # Fresh re-read sees stale -> still timed out.
+    assert (
+        await svc._session_still_timed_out(sid, timeout_seconds=1, max_time_window=None)
+        is True
+    )
+    # A message lands, refreshing activity.
+    sess.last_activity_at = datetime.now(UTC)
+    await db_session.flush()
+    # Fresh re-read sees recent -> no longer timed out -> sweeper must skip.
+    assert (
+        await svc._session_still_timed_out(sid, timeout_seconds=1, max_time_window=None)
+        is False
+    )
+
+
 @pytest.mark.asyncio
 async def test_edit_message_or_raise_succeeds(msg_setup: dict) -> None:
     svc = msg_setup["svc"]