fix(gateway): preserve update notification retry state

gateway/run.py

@@ -11203,16 +11203,30 @@ async def _flush_buffer() -> None:
                     exit_code_raw = exit_code_path.read_text().strip() or "1"
                     exit_code = int(exit_code_raw)
                     if exit_code == 0:
-                        await adapter.send(chat_id, "✅ Hermes update finished.", metadata=metadata)
+                        result = await adapter.send(
+                            chat_id,
+                            "✅ Hermes update finished.",
+                            metadata=metadata,
+                        )
                     else:
-                        await adapter.send(
+                        result = await adapter.send(
                             chat_id,
                             "❌ Hermes update failed (exit code {}).".format(exit_code),
                             metadata=metadata,
                         )
+                    if result is not None and getattr(result, "success", True) is False:
+                        logger.warning(
+                            "Update final notification to %s was not delivered: %s",
+                            session_key,
+                            getattr(result, "error", "send returned success=False"),
+                        )
+                        await asyncio.sleep(poll_interval)
+                        continue
                     logger.info("Update finished (exit=%s), notified %s", exit_code, session_key)
                 except Exception as e:
                     logger.warning("Update final notification failed: %s", e)
+                    await asyncio.sleep(poll_interval)
+                    continue
 
                 # Cleanup
                 for p in (pending_path, claimed_path, output_path,
@@ -11402,7 +11416,25 @@ async def _send_update_notification(self) -> bool:
                     msg = "✅ Hermes update finished successfully."
                 else:
                     msg = "❌ Hermes update failed. Check the gateway logs or run `hermes update` manually for details."
-                await adapter.send(chat_id, msg, metadata=metadata)
+                result = await adapter.send(chat_id, msg, metadata=metadata)
+                if result is not None and getattr(result, "success", True) is False:
+                    logger.warning(
+                        "Post-update notification to %s:%s was not delivered: %s",
+                        platform_str,
+                        chat_id,
+                        getattr(result, "error", "send returned success=False"),
+                    )
+                    cleanup = False
+                    active_pending_path = pending_path
+                    try:
+                        if claimed_path.exists():
+                            claimed_path.replace(pending_path)
+                    except OSError as move_err:
+                        logger.warning(
+                            "Failed to preserve post-update notification markers: %s",
+                            move_err,
+                        )
+                    return False
                 logger.info(
                     "Sent post-update notification to %s:%s (exit=%s)",
                     platform_str,

tests/gateway/test_update_command.py

@@ -11,7 +11,7 @@
 import pytest
 
 from gateway.config import Platform
-from gateway.platforms.base import MessageEvent
+from gateway.platforms.base import MessageEvent, SendResult
 from gateway.session import SessionSource
 
 
@@ -763,6 +763,40 @@ async def test_cleans_up_files_after_notification(self, tmp_path):
         assert not output_path.exists()
         assert not exit_code_path.exists()
 
+    @pytest.mark.asyncio
+    async def test_send_result_failure_preserves_markers_for_retry(self, tmp_path):
+        """SendResult(success=False) não confirma entrega e mantém retry pendente."""
+        runner = _make_runner()
+        hermes_home = tmp_path / "hermes"
+        hermes_home.mkdir()
+
+        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({
+            "platform": "telegram", "chat_id": "111", "user_id": "222",
+        }))
+        output_path.write_text("✓ Done")
+        exit_code_path.write_text("0")
+
+        mock_adapter = AsyncMock()
+        mock_adapter.send.return_value = SendResult(
+            success=False,
+            error="telegram timed out",
+            retryable=True,
+        )
+        runner.adapters = {Platform.TELEGRAM: mock_adapter}
+
+        with patch("gateway.run._hermes_home", hermes_home):
+            result = await runner._send_update_notification()
+
+        assert result is False
+        mock_adapter.send.assert_called_once()
+        assert pending_path.exists()
+        assert output_path.exists()
+        assert exit_code_path.exists()
+        assert not (hermes_home / ".update_pending.claimed.json").exists()
+
     @pytest.mark.asyncio
     async def test_cleans_up_on_error(self, tmp_path):
         """Files are cleaned up even if notification fails."""

tests/gateway/test_update_streaming.py

@@ -16,7 +16,7 @@
 import pytest
 
 from gateway.config import Platform
-from gateway.platforms.base import MessageEvent
+from gateway.platforms.base import MessageEvent, SendResult
 from gateway.session import SessionSource
 
 
@@ -412,6 +412,41 @@ async def test_cleans_up_on_completion(self, tmp_path):
         assert not output_path.exists()
         assert not exit_code_path.exists()
 
+    @pytest.mark.asyncio
+    async def test_keeps_markers_when_final_notification_send_fails(self, tmp_path):
+        """Falha retornada por adapter.send deve preservar estado para retry."""
+        runner = _make_runner()
+        hermes_home = tmp_path / "hermes"
+        hermes_home.mkdir()
+
+        pending = {"platform": "telegram", "chat_id": "111", "user_id": "222",
+                   "session_key": "agent:main:telegram:dm:111"}
+        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("done\n")
+        exit_code_path.write_text("0")
+
+        mock_adapter = AsyncMock()
+        mock_adapter.send.return_value = SendResult(
+            success=False,
+            error="telegram timed out",
+            retryable=True,
+        )
+        runner.adapters = {Platform.TELEGRAM: mock_adapter}
+
+        with patch("gateway.run._hermes_home", hermes_home):
+            await runner._watch_update_progress(
+                poll_interval=0.05,
+                stream_interval=0.1,
+                timeout=0.15,
+            )
+
+        assert pending_path.exists()
+        assert output_path.exists()
+        assert exit_code_path.exists()
+
     @pytest.mark.asyncio
     async def test_failure_exit_code(self, tmp_path):
         """Non-zero exit code sends failure message."""