fix(chat): clarify missing-location search requests

backend/server/chat/tests.py

@@ -3,6 +3,7 @@ from unittest.mock import patch
 
 from django.contrib.auth import get_user_model
 from django.test import TestCase
+from rest_framework.test import APITestCase
 
 from adventures.models import Collection, CollectionItineraryItem
 from chat.agent_tools import add_to_itinerary, get_trip_details
@@ -146,3 +147,98 @@ class ChatViewSetToolValidationBoundaryTests(TestCase):
                 json.dumps({"error": error_text})
             )
         )
+
+    def test_search_places_missing_location_error_detected_for_clarification(self):
+        self.assertTrue(
+            ChatViewSet._is_search_places_missing_location_required_error(
+                "search_places",
+                {"error": "location is required"},
+            )
+        )
+
+    def test_non_search_places_required_error_not_detected_for_clarification(self):
+        self.assertFalse(
+            ChatViewSet._is_search_places_missing_location_required_error(
+                "web_search",
+                {"error": "query is required"},
+            )
+        )
+
+
+class ChatViewSetSearchPlacesClarificationTests(APITestCase):
+    @patch("chat.views.execute_tool")
+    @patch("chat.views.stream_chat_completion")
+    @patch("integrations.utils.auto_profile.update_auto_preference_profile")
+    def test_missing_search_place_location_streams_clarifying_content(
+        self,
+        _mock_auto_profile,
+        mock_stream_chat_completion,
+        mock_execute_tool,
+    ):
+        user = User.objects.create_user(
+            username="chat-clarify-user",
+            email="chat-clarify-user@example.com",
+            password="password123",
+        )
+        self.client.force_authenticate(user=user)
+
+        conversation_response = self.client.post(
+            "/api/chat/conversations/",
+            {"title": "Clarification Test"},
+            format="json",
+        )
+        self.assertEqual(conversation_response.status_code, 201)
+        conversation_id = conversation_response.json()["id"]
+
+        async def mock_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"
+
+        mock_stream_chat_completion.side_effect = mock_stream
+        mock_execute_tool.return_value = {"error": "location is required"}
+
+        response = self.client.post(
+            f"/api/chat/conversations/{conversation_id}/send_message/",
+            {"message": "Find good places"},
+            format="json",
+        )
+
+        self.assertEqual(response.status_code, 200)
+        self.assertEqual(response["Content-Type"], "text/event-stream")
+
+        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: ")
+        ]
+
+        done_count = sum(1 for payload in payload_lines if payload == "[DONE]")
+        self.assertEqual(done_count, 1)
+
+        json_payloads = [
+            json.loads(payload) for payload in payload_lines if payload != "[DONE]"
+        ]
+        self.assertTrue(any("content" in payload for payload in json_payloads))
+        self.assertFalse(
+            any(payload.get("error_category") for payload in json_payloads)
+        )
+
+        content_payload = next(
+            payload for payload in json_payloads if "content" in payload
+        )
+        self.assertIn("specific location", content_payload["content"].lower())
+
+        clarifying_message = (
+            user.chat_conversations.get(id=conversation_id)
+            .messages.filter(role="assistant")
+            .order_by("created_at")
+            .last()
+        )
+        self.assertIsNotNone(clarifying_message)
+        self.assertIn("specific location", clarifying_message.content.lower())