fix(gateway): surface actionable message for local model server connection errors

gateway/run.py

@@ -407,6 +407,25 @@ def _gateway_surface_passes_raw_text(platform: Any) -> bool:
     re.IGNORECASE,
 )
 
+_GATEWAY_CONNECTION_ERROR_RE = re.compile(
+    r"("
+    r"(?:\w+\.)?(?:api\s*)?connection\s*(?:error|timeout)"
+    r"|(?:\w+\.)?connect\s*(?:error|timeout)"
+    r"|connection\s+refused"
+    r"|connection\s+reset"
+    r"|connection\s+aborted"
+    r"|actively\s+refused"
+    r"|winerror\s+10061"
+    r"|errno\s+111"
+    r"|no\s+route\s+to\s+host"
+    r"|network\s+is\s+unreachable"
+    r"|cannot\s+connect"
+    r"|failed\s+to\s+establish"
+    r"|could\s+not\s+connect"
+    r")",
+    re.IGNORECASE,
+)
+
 _GATEWAY_SECRET_PATTERNS = (
     re.compile(r"\bsk-[A-Za-z0-9][A-Za-z0-9_\-]{12,}\b"),
     re.compile(r"\bgh[pousr]_[A-Za-z0-9_]{20,}\b"),
@@ -665,7 +684,6 @@ def _format_exec_approval_fallback(
         + ", ".join(choices[:-1]) + f", or {choices[-1]}."
     )
 
-
 def _gateway_provider_error_reply(text: str) -> str:
     """Map raw provider/API errors to a short user-safe Telegram reply."""
     if _GATEWAY_AUTH_ERROR_RE.search(text):
@@ -680,6 +698,11 @@ def _gateway_provider_error_reply(text: str) -> str:
         )
     if _GATEWAY_RATE_LIMIT_RE.search(text):
         return "⏱️ The model provider is rate-limiting requests. Please wait a moment and try again."
+    if _GATEWAY_CONNECTION_ERROR_RE.search(text):
+        return (
+            "⚠️ The model server is not responding — it looks like the configured "
+            "model endpoint is not running or is unreachable."
+        )
     return (
         "⚠️ The model provider failed after retries. I kept raw provider details "
         "out of chat; check gateway logs for diagnostics."
@@ -696,6 +719,15 @@ def _gateway_provider_error_reply(text: str) -> str:
     r"|http\s*\d{3}\b"
     r"|incorrect\s+api\s+key"
     r"|invalid\s+api\s+key"
+    r"|(?:\w+\.)?(?:api\s*)?connection\s*(?:error|timeout)"
+    r"|(?:\w+\.)?connect\s*(?:error|timeout)"
+    r"|connection\s+refused"
+    r"|connection\s+reset"
+    r"|connection\s+aborted"
+    r"|actively\s+refused"
+    r"|winerror\s+10061"
+    r"|errno\s+111"
+    r"|all\s+connection\s+attempts\s+failed"
     r")",
     re.IGNORECASE,
 )

tests/gateway/test_local_model_connection_reply.py

@@ -0,0 +1,63 @@
+"""Regression tests for #86570: gateway provider error connection messaging."""
+
+import pytest
+
+from gateway.run import (
+    _GATEWAY_CONNECTION_ERROR_RE,
+    _gateway_provider_error_reply,
+    _looks_like_gateway_provider_error,
+)
+
+
+class TestGatewayConnectionErrorReply:
+    def test_connection_error_strings_produce_specific_reply(self):
+        samples = [
+            "openai.APIConnectionError",
+            "httpx.ConnectError: connection refused",
+            "ConnectionError: [WinError 10061] No connection could be made",
+            "Errno 111 Connection refused",
+            "All connection attempts failed: Connection refused",
+        ]
+        for text in samples:
+            assert _looks_like_gateway_provider_error(text), text
+            reply = _gateway_provider_error_reply(text)
+            assert "not responding" in reply.lower(), text
+            assert "not running or is unreachable" in reply, text
+
+    def test_broad_connection_phrases_still_map_once_classified(self):
+        """Reply selector keeps the full phrase set; the gate does not."""
+        for text in (
+            "cannot connect to http://127.0.0.1:8033/v1",
+            "failed to establish a new connection",
+        ):
+            reply = _gateway_provider_error_reply(text)
+            assert "not running or is unreachable" in reply, text
+
+    def test_prose_cannot_connect_is_not_a_provider_error(self):
+        text = (
+            "cannot connect to the office VPN from this cafe, "
+            "so I used the backup notes instead"
+        )
+        assert not _looks_like_gateway_provider_error(text)
+
+    def test_other_errors_keep_generic_reply(self):
+        for text in (
+            "RuntimeError: model returned empty content",
+            "Exception: unknown provider",
+            "HTTP 500 internal server error",
+        ):
+            if _looks_like_gateway_provider_error(text):
+                reply = _gateway_provider_error_reply(text)
+                assert "not running or is unreachable" not in reply, text
+
+    def test_connection_regex_does_not_match_non_connection_error(self):
+        assert not _GATEWAY_CONNECTION_ERROR_RE.search("Rate limited after 3 retries")
+        assert not _GATEWAY_CONNECTION_ERROR_RE.search("Provider authentication failed")
+
+    def test_auth_and_rate_limit_preserved(self):
+        assert "authentication" in _gateway_provider_error_reply(
+            "provider authentication failed"
+        ).lower()
+        assert "rate-limiting" in _gateway_provider_error_reply(
+            "rate limited after 3 retries"
+        ).lower()