fix(gateway): keep pending /update completion notifications until the target platform reconnects

gateway/run.py

@@ -15142,10 +15142,15 @@ class GatewayRunner:
 
         if not adapter or not chat_id:
             logger.warning("Update watcher: cannot resolve adapter/chat_id, falling back to completion-only")
-            # Fall back to old behavior: wait for exit code and send final notification
+            # Fall back to completion-only: wait for the exit code and send the
+            # final notification. _send_update_notification re-resolves the
+            # adapter on every call, so when the target platform is still
+            # reconnecting it returns False and keeps the markers. Keep polling
+            # until it actually delivers (returns True) instead of giving up
+            # after the first completion check — otherwise a platform that
+            # reconnects a few seconds after completion never gets notified.
             while (pending_path.exists() or claimed_path.exists()) and loop.time() < deadline:
-                if exit_code_path.exists():
-                    await self._send_update_notification()
+                if exit_code_path.exists() and await self._send_update_notification():
                     return
                 await asyncio.sleep(poll_interval)
             if (pending_path.exists() or claimed_path.exists()) and not exit_code_path.exists():
@@ -15359,6 +15364,24 @@ class GatewayRunner:
             platform = Platform(platform_str)
             adapter = self.adapters.get(platform)
 
+            if not adapter and chat_id:
+                # The update finished, but the target platform has not
+                # reconnected yet (common right after the restart that
+                # `hermes update` triggers). Treating "adapter missing" as a
+                # definitive skip would delete the markers and silently lose the
+                # completion notification — the user never learns whether the
+                # update succeeded or timed out. Preserve the markers instead so
+                # a later retry (the watcher poll loop, or the next gateway
+                # startup) can deliver the result once the adapter is back.
+                logger.info(
+                    "Update notification deferred: %s adapter not connected yet",
+                    platform_str,
+                )
+                cleanup = False
+                active_pending_path = pending_path
+                claimed_path.replace(pending_path)
+                return False
+
             if adapter and chat_id:
                 metadata = self._thread_metadata_for_target(
                     platform,

tests/gateway/test_update_command.py

@@ -661,8 +661,14 @@ class TestSendUpdateNotification:
         assert not pending_path.exists()
 
     @pytest.mark.asyncio
-    async def test_no_adapter_for_platform(self, tmp_path):
-        """Does not crash if the platform adapter is not connected."""
+    async def test_no_adapter_for_platform_preserves_markers(self, tmp_path):
+        """A finished update whose platform is offline keeps its markers.
+
+        When the target platform's adapter has not reconnected yet, dropping
+        the completion markers would silently lose the notification. Instead the
+        call defers (returns False) and leaves every marker on disk so a later
+        retry can deliver once the platform is back.
+        """
         runner = _make_runner()
         hermes_home = tmp_path / "hermes"
         hermes_home.mkdir()
@@ -680,13 +686,62 @@ class TestSendUpdateNotification:
         runner.adapters = {Platform.TELEGRAM: mock_adapter}
 
         with patch("gateway.run._hermes_home", hermes_home):
-            await runner._send_update_notification()
+            result = await runner._send_update_notification()
 
-        # send should not have been called (wrong platform)
+        # No send (wrong platform offline) and the result is deferred.
+        assert result is False
         mock_adapter.send.assert_not_called()
-        # Files should still be cleaned up
+        # Markers are preserved for a later retry — NOT cleaned up.
+        assert pending_path.exists()
+        assert output_path.exists()
+        assert exit_code_path.exists()
+        # The marker stays in its canonical pending location (claim restored).
+        assert not (hermes_home / ".update_pending.claimed.json").exists()
+
+    @pytest.mark.asyncio
+    async def test_deferred_notification_delivers_after_reconnect(self, tmp_path):
+        """A deferred completion is delivered once the platform reconnects.
+
+        Regression for the late-reconnect /update bug: the update finishes while
+        the target platform is offline, the markers survive the deferral, and
+        the next call (after the adapter is registered) delivers the result and
+        cleans up — exactly once.
+        """
+        runner = _make_runner()
+        hermes_home = tmp_path / "hermes"
+        hermes_home.mkdir()
+
+        pending = {"platform": "discord", "chat_id": "111", "user_id": "222"}
+        pending_path = hermes_home / ".update_pending.json"
+        output_path = hermes_home / ".update_output.txt"
+        exit_code_path = hermes_home / ".update_exit_code"
+        pending_path.write_text(json.dumps(pending))
+        output_path.write_text("✓ Update complete!")
+        exit_code_path.write_text("0")
+
+        # First pass: target platform (discord) is still offline → defer.
+        with patch("gateway.run._hermes_home", hermes_home):
+            first = await runner._send_update_notification()
+
+        assert first is False
+        assert pending_path.exists()
+
+        # Platform reconnects: the reconnect watcher adds the adapter back.
+        mock_adapter = AsyncMock()
+        runner.adapters = {Platform.DISCORD: mock_adapter}
+
+        with patch("gateway.run._hermes_home", hermes_home):
+            second = await runner._send_update_notification()
+
+        assert second is True
+        mock_adapter.send.assert_called_once()
+        sent_text = mock_adapter.send.call_args[0][1]
+        assert "Update complete" in sent_text
+        # Now everything is cleaned up — no duplicate deliveries possible.
         assert not pending_path.exists()
+        assert not output_path.exists()
         assert not exit_code_path.exists()
+        assert not (hermes_home / ".update_pending.claimed.json").exists()
 
 
 # ---------------------------------------------------------------------------

tests/gateway/test_update_streaming.py

@@ -439,30 +439,49 @@ class TestWatchUpdateProgress:
         assert "failed" in all_sent.lower()
 
     @pytest.mark.asyncio
-    async def test_falls_back_when_adapter_unavailable(self, tmp_path):
-        """Falls back to legacy notification when adapter can't be resolved."""
+    async def test_falls_back_and_delivers_after_reconnect(self, tmp_path):
+        """Completion-only fallback waits for the platform to reconnect.
+
+        When the target adapter isn't connected at watcher start, the watcher
+        must keep the markers and retry until the platform reconnects, then
+        deliver the completion notification — rather than dropping it on the
+        first completion check (the late-reconnect /update bug).
+        """
         runner = _make_runner()
         hermes_home = tmp_path / "hermes"
         hermes_home.mkdir()
 
-        # Platform doesn't match any adapter
+        # Target platform (discord) isn't connected yet; the update is finished.
         pending = {"platform": "discord", "chat_id": "111", "user_id": "222"}
-        (hermes_home / ".update_pending.json").write_text(json.dumps(pending))
+        pending_path = hermes_home / ".update_pending.json"
+        pending_path.write_text(json.dumps(pending))
         (hermes_home / ".update_output.txt").write_text("done\n")
         (hermes_home / ".update_exit_code").write_text("0")
 
-        # Only telegram adapter available
-        mock_adapter = AsyncMock()
-        runner.adapters = {Platform.TELEGRAM: mock_adapter}
+        # Only telegram is connected at first.
+        runner.adapters = {Platform.TELEGRAM: AsyncMock()}
+
+        discord_adapter = AsyncMock()
+
+        async def reconnect_discord():
+            # The platform reconnect watcher registers discord mid-poll.
+            await asyncio.sleep(0.3)
+            runner.adapters[Platform.DISCORD] = discord_adapter
 
         with patch("gateway.run._hermes_home", hermes_home):
+            task = asyncio.create_task(reconnect_discord())
             await runner._watch_update_progress(
                 poll_interval=0.1,
                 stream_interval=0.2,
                 timeout=5.0,
             )
+            await task
 
-        # Should not crash; legacy notification handles this case
+        # The completion was delivered to discord once it reconnected...
+        discord_adapter.send.assert_called_once()
+        # ...and the markers are cleaned up after successful delivery.
+        assert not pending_path.exists()
+        assert not (hermes_home / ".update_exit_code").exists()
 
     @pytest.mark.asyncio
     async def test_prompt_forwarded_only_once(self, tmp_path):