fix(chat): fix location clarification loop and test isolation bugs

- Add _COMMAND_VERBS guard to _is_likely_location_reply() so messages
  starting with imperative verbs (find, search, show, get, ...) are not
  mistakenly treated as user location replies. This prevented 'Find
  good places' from being used as a retry location, which was causing
  the clarification path to never fire and the tool loop to exhaust
  MAX_ALL_FAILURE_ROUNDS instead.
- Extract city from comma-delimited fallback address strings when
  city/country FKs are absent, e.g. 'Little Turnstile 6, London'
  → 'London', so context-based location retry works for manually-
  entered itinerary stops without geocoded FK data.
- Add attempted_location_retry flag: if retry was attempted but all
  retry attempts failed, convert result to an execution failure rather
  than emitting a clarification prompt (user already provided context
  via their itinerary).
- Fix test assertion ordering in test_collection_context_retry_extracts_
  city_from_fallback_address: streaming_content must be consumed before
  checking mock call counts since StreamingHttpResponse is lazy.

AGENTS.md

@@ -74,6 +74,8 @@ Run in this order:
 - Chat providers: dynamic catalog from `GET /api/chat/providers/`; configured in `CHAT_PROVIDER_CONFIG`
 - Chat model override: dropdown selector fed by `GET /api/chat/providers/{provider}/models/`; persisted in `localStorage` key `voyage_chat_model_prefs`; backend accepts optional `model` param in `send_message`
 - Chat context: collection chats inject collection UUID + multi-stop itinerary context; system prompt guides `get_trip_details`-first reasoning and confirms only before first `add_to_itinerary`; `search_places` has a deterministic context-retry fallback — when the LLM omits `location`, the backend retries using the trip destination or first itinerary stop before asking the user for clarification; a dining-intent heuristic infers `category="food"` from user messages when the LLM omits category for restaurant/dining requests
+- `itinerary_stops` extraction: when `city`/`country` FK is null, city is extracted from the last non-numeric segment of a comma-separated address (e.g. `"Little Turnstile 6, London"` → `"London"`); ensures `trip_context_location` is always a geocodable city name, not a street address.
+- After itinerary context retries: if all retries fail, result is converted to an execution failure rather than triggering a clarification prompt — the user is never asked for a location they already implied via collection context.
 - Chat tool output: `role=tool` messages hidden from display; tool outputs render as concise summaries; persisted tool rows reconstructed on reload via `rebuildConversationMessages()`; tool results are deduplicated by `tool_call_id` at three layers — rebuild from persisted rows (discards server-side pre-populated `tool_results`), SSE ingestion (`appendToolResultDedup`), and render-time (`uniqueToolResultsByCallId`)
 - Chat error surfacing: `_safe_error_payload()` maps LiteLLM exceptions to sanitized user-safe categories (never forwards raw `exc.message`); `execute_tool()` catch-all returns a generic sanitized message (never raw `str(exc)`)
 - Invalid tool calls (missing required args) are detected and short-circuited with a user-visible error — not replayed into history

backend/server/chat/tests.py

@@ -563,6 +563,70 @@ class ChatViewSetSearchPlacesClarificationTests(APITransactionTestCase):
         self.assertEqual(second_call_kwargs.get("category"), "food")
         self.assertEqual(second_call_kwargs.get("location"), "Rome, Italy")
 
+    @patch("chat.views.execute_tool")
+    @patch("chat.views.stream_chat_completion")
+    @patch("integrations.utils.auto_profile.update_auto_preference_profile")
+    def test_collection_context_retry_extracts_city_from_fallback_address(
+        self,
+        _mock_auto_profile,
+        mock_stream_chat_completion,
+        mock_execute_tool,
+    ):
+        user = User.objects.create_user(
+            username="chat-city-extract-user",
+            email="chat-city-extract-user@example.com",
+            password="password123",
+        )
+        self.client.force_authenticate(user=user)
+
+        collection = Collection.objects.create(user=user, name="London Food Trip")
+        trip_stop = Location.objects.create(
+            user=user,
+            name="Turnstile",
+            location="Little Turnstile 6, London",
+        )
+        collection.locations.add(trip_stop)
+
+        conversation_response = self.client.post(
+            "/api/chat/conversations/",
+            {"title": "Fallback City Extraction Test"},
+            format="json",
+        )
+        self.assertEqual(conversation_response.status_code, 201)
+        conversation_id = conversation_response.json()["id"]
+
+        async def first_stream(*args, **kwargs):
+            yield 'data: {"tool_calls": [{"index": 0, "id": "call_1", "type": "function", "function": {"name": "search_places", "arguments": "{}"}}]}\n\n'
+            yield "data: [DONE]\n\n"
+
+        async def second_stream(*args, **kwargs):
+            yield 'data: {"content": "Here are options in London."}\n\n'
+            yield "data: [DONE]\n\n"
+
+        mock_stream_chat_completion.side_effect = [first_stream(), second_stream()]
+        mock_execute_tool.side_effect = [
+            {"error": "location is required"},
+            {"results": [{"name": "Rules Restaurant"}]},
+        ]
+
+        response = self.client.post(
+            f"/api/chat/conversations/{conversation_id}/send_message/",
+            {
+                "message": "Find restaurants",
+                "collection_id": str(collection.id),
+                "collection_name": collection.name,
+            },
+            format="json",
+        )
+
+        self.assertEqual(response.status_code, 200)
+        # Consume the streaming response before checking mock call counts;
+        # the event_stream generator only runs when streaming_content is iterated.
+        list(response.streaming_content)
+        self.assertEqual(mock_execute_tool.call_count, 2)
+        second_call_kwargs = mock_execute_tool.call_args_list[1].kwargs
+        self.assertEqual(second_call_kwargs.get("location"), "London")
+
     @patch("chat.views.execute_tool")
     @patch("chat.views.stream_chat_completion")
     @patch("integrations.utils.auto_profile.update_auto_preference_profile")
@@ -857,3 +921,79 @@ class ChatViewSetToolExecutionFailureLoopTests(APITransactionTestCase):
         )
         self.assertEqual(mock_stream_chat_completion.call_count, 1)
         self.assertEqual(mock_execute_tool.call_count, 1)
+
+    @patch("chat.views.execute_tool")
+    @patch("chat.views.stream_chat_completion")
+    @patch("integrations.utils.auto_profile.update_auto_preference_profile")
+    def test_context_retry_failure_does_not_emit_location_clarification(
+        self,
+        _mock_auto_profile,
+        mock_stream_chat_completion,
+        mock_execute_tool,
+    ):
+        user = User.objects.create_user(
+            username="chat-retry-no-clarify-user",
+            email="chat-retry-no-clarify-user@example.com",
+            password="password123",
+        )
+        self.client.force_authenticate(user=user)
+
+        conversation_response = self.client.post(
+            "/api/chat/conversations/",
+            {"title": "Retry Failure No Clarify Test"},
+            format="json",
+        )
+        self.assertEqual(conversation_response.status_code, 201)
+        conversation_id = conversation_response.json()["id"]
+
+        async def failing_stream(*args, **kwargs):
+            yield 'data: {"tool_calls": [{"index": 0, "id": "call_s", "type": "function", "function": {"name": "search_places", "arguments": "{}"}}]}\n\n'
+            yield "data: [DONE]\n\n"
+
+        mock_stream_chat_completion.side_effect = failing_stream
+        mock_execute_tool.side_effect = [
+            {"error": "location is required"},
+            {"error": "location is required"},
+            {"error": "location is required"},
+            {"error": "location is required"},
+            {"error": "location is required"},
+            {"error": "location is required"},
+        ]
+
+        response = self.client.post(
+            f"/api/chat/conversations/{conversation_id}/send_message/",
+            {
+                "message": "Find restaurants",
+                "destination": "Lisbon, Portugal",
+            },
+            format="json",
+        )
+
+        self.assertEqual(response.status_code, 200)
+        chunks = [
+            chunk.decode("utf-8")
+            if isinstance(chunk, (bytes, bytearray))
+            else str(chunk)
+            for chunk in response.streaming_content
+        ]
+        payload_lines = [
+            chunk.strip()[len("data: ") :]
+            for chunk in chunks
+            if chunk.strip().startswith("data: ")
+        ]
+        json_payloads = [
+            json.loads(payload) for payload in payload_lines if payload != "[DONE]"
+        ]
+
+        self.assertTrue(
+            any(
+                payload.get("error_category") == "tool_execution_error"
+                for payload in json_payloads
+            )
+        )
+        self.assertFalse(
+            any(
+                "specific location" in payload.get("content", "").lower()
+                for payload in json_payloads
+            )
+        )

backend/server/chat/views/__init__.py

@@ -326,8 +326,35 @@ class ChatViewSet(viewsets.ModelViewSet):
 
         return None
 
-    @staticmethod
-    def _is_likely_location_reply(user_content):
+    # Verbs that indicate a command/request rather than a location reply.
+    _COMMAND_VERBS = frozenset(
+        [
+            "find",
+            "search",
+            "show",
+            "get",
+            "look",
+            "give",
+            "tell",
+            "help",
+            "recommend",
+            "suggest",
+            "list",
+            "fetch",
+            "what",
+            "where",
+            "which",
+            "who",
+            "how",
+            "can",
+            "could",
+            "would",
+            "please",
+        ]
+    )
+
+    @classmethod
+    def _is_likely_location_reply(cls, user_content):
         if not isinstance(user_content, str):
             return False
 
@@ -345,6 +372,12 @@ class ChatViewSet(viewsets.ModelViewSet):
         if len(parts) > 6:
             return False
 
+        # Exclude messages that start with a command/request verb — those are
+        # original requests, not replies to a "where?" clarification prompt.
+        first_word = parts[0].lower().rstrip(".,!;:")
+        if first_word in cls._COMMAND_VERBS:
+            return False
+
         return bool(re.search(r"[a-z0-9]", normalized, re.IGNORECASE))
 
     @action(detail=True, methods=["post"])
@@ -445,8 +478,21 @@ class ChatViewSet(viewsets.ModelViewSet):
                     fallback_name = (location.location or location.name or "").strip()
                     if not fallback_name:
                         continue
-                    stop_label = fallback_name
-                    stop_key = f"name:{fallback_name.lower()}"
+                    # When city/country FKs are not set, try to extract a geocodable
+                    # city name from a comma-separated address string.
+                    # e.g. "Little Turnstile 6, London" → "London"
+                    # e.g. "Kingsway 58, London" → "London"
+                    if "," in fallback_name:
+                        parts = [p.strip() for p in fallback_name.split(",")]
+                        # Last non-empty, non-purely-numeric segment is typically the city
+                        city_hint = next(
+                            (p for p in reversed(parts) if p and not p.isdigit()),
+                            None,
+                        )
+                        stop_label = city_hint if city_hint else fallback_name
+                    else:
+                        stop_label = fallback_name
+                    stop_key = f"name:{stop_label.lower()}"
 
                 if stop_key in seen_stops:
                     continue
@@ -595,6 +641,7 @@ class ChatViewSet(viewsets.ModelViewSet):
                             **prepared_arguments,
                         )
 
+                        attempted_location_retry = False
                         if self._is_search_places_location_retry_candidate_error(
                             function_name,
                             result,
@@ -616,6 +663,7 @@ class ChatViewSet(viewsets.ModelViewSet):
                                 ):
                                     continue
                                 seen_retry_locations.add(normalized_retry_location)
+                                attempted_location_retry = True
 
                                 retry_arguments = dict(prepared_arguments)
                                 retry_arguments["location"] = retry_location
@@ -644,6 +692,17 @@ class ChatViewSet(viewsets.ModelViewSet):
                                     }
                                     break
 
+                            # If we attempted context retries but all failed, convert
+                            # to an execution failure so we never ask the user for a
+                            # location they already implied via itinerary context.
+                            if (
+                                attempted_location_retry
+                                and self._is_required_param_tool_error(result)
+                            ):
+                                result = {
+                                    "error": "Could not search places at the provided itinerary locations"
+                                }
+
                         if self._is_required_param_tool_error(result):
                             assistant_message_kwargs = {
                                 "conversation": conversation,
@@ -665,9 +724,12 @@ class ChatViewSet(viewsets.ModelViewSet):
                                     thread_sensitive=True,
                                 )(**tool_message)
 
-                            if self._is_search_places_missing_location_required_error(
-                                function_name,
-                                result,
+                            if (
+                                not attempted_location_retry
+                                and self._is_search_places_missing_location_required_error(
+                                    function_name,
+                                    result,
+                                )
                             ):
                                 clarification_content = self._build_search_places_location_clarification_message()
                                 await sync_to_async(