fix: persist assistant tool errors and markdown

backend/server/chat/tests.py

@@ -8,6 +8,7 @@ import requests as _requests
 from django.contrib.auth import get_user_model
 from django.contrib.contenttypes.models import ContentType
 from django.test import TestCase
+from rest_framework.exceptions import PermissionDenied, ValidationError
 from rest_framework.test import APITransactionTestCase
 
 from adventures.models import Collection, CollectionItineraryItem, Location, Visit
@@ -459,6 +460,63 @@ class ChatAgentToolItineraryManagementTests(TestCase):
         self.assertEqual(remove_result, {"error": "Trip not found"})
         self.assertEqual(update_result, {"error": "Trip not found"})
 
+    @patch("chat.agent_tools.reorder_itinerary_items")
+    def test_move_itinerary_item_returns_validation_error_from_reorder(
+        self,
+        mock_reorder_itinerary_items,
+    ):
+        mock_reorder_itinerary_items.side_effect = ValidationError(
+            {
+                "items": (
+                    "Item abc date 2026-05-30 is before collection start date "
+                    "2026-06-01."
+                )
+            }
+        )
+
+        self.collection.start_date = date(2026, 6, 1)
+        self.collection.save(update_fields=["start_date"])
+
+        result = move_itinerary_item(
+            self.owner,
+            collection_id=str(self.collection.id),
+            itinerary_item_id=str(self.day1_item.id),
+            date="2026-06-02",
+            order=0,
+        )
+
+        self.assertEqual(
+            result,
+            {
+                "error": (
+                    "Item abc date 2026-05-30 is before collection start date "
+                    "2026-06-01."
+                )
+            },
+        )
+
+    @patch("chat.agent_tools.reorder_itinerary_items")
+    def test_move_itinerary_item_returns_permission_error_from_reorder(
+        self,
+        mock_reorder_itinerary_items,
+    ):
+        mock_reorder_itinerary_items.side_effect = PermissionDenied(
+            "You do not have permission to modify items in this collection."
+        )
+
+        result = move_itinerary_item(
+            self.owner,
+            collection_id=str(self.collection.id),
+            itinerary_item_id=str(self.day1_item.id),
+            date="2026-06-02",
+            order=0,
+        )
+
+        self.assertEqual(
+            result,
+            {"error": "You do not have permission to modify items in this collection."},
+        )
+
 
 class ChatViewSetToolValidationBoundaryTests(TestCase):
     def test_trip_context_destination_summary_normalizes_to_first_segment(self):
@@ -589,6 +647,70 @@ class ChatViewSetToolValidationBoundaryTests(TestCase):
 
 
 class ChatViewSetSearchPlacesClarificationTests(APITransactionTestCase):
+    @patch("chat.views.stream_chat_completion")
+    @patch("integrations.utils.auto_profile.update_auto_preference_profile")
+    def test_collection_context_includes_uuid_guidance_for_existing_item_tools(
+        self,
+        _mock_auto_profile,
+        mock_stream_chat_completion,
+    ):
+        user = User.objects.create_user(
+            username="chat-context-tool-guidance-user",
+            email="chat-context-tool-guidance-user@example.com",
+            password="password123",
+        )
+        self.client.force_authenticate(user=user)
+
+        collection = Collection.objects.create(user=user, name="Paris Trip")
+
+        conversation_response = self.client.post(
+            "/api/chat/conversations/",
+            {"title": "Context Tool Guidance Test"},
+            format="json",
+        )
+        self.assertEqual(conversation_response.status_code, 201)
+        conversation_id = conversation_response.json()["id"]
+
+        async def stream_noop(*args, **kwargs):
+            yield "data: [DONE]\n\n"
+
+        mock_stream_chat_completion.side_effect = stream_noop
+
+        response = self.client.post(
+            f"/api/chat/conversations/{conversation_id}/send_message/",
+            {
+                "message": "Move my first stop to day 2",
+                "collection_id": str(collection.id),
+                "collection_name": collection.name,
+            },
+            format="json",
+        )
+
+        self.assertEqual(response.status_code, 200)
+        list(response.streaming_content)
+
+        stream_call_messages = mock_stream_chat_completion.call_args.args[1]
+        system_message = next(
+            message for message in stream_call_messages if message["role"] == "system"
+        )
+        normalized_system_content = system_message["content"].lower()
+        self.assertIn(
+            (
+                "use this exact collection_id for get_trip_details, "
+                "add_to_itinerary, move_itinerary_item, remove_itinerary_item, "
+                "and update_location_details"
+            ),
+            normalized_system_content,
+        )
+        self.assertIn(
+            (
+                "call get_trip_details first before move_itinerary_item, "
+                "remove_itinerary_item, or update_location_details when exact IDs "
+                "are needed"
+            ).lower(),
+            normalized_system_content,
+        )
+
     @patch("chat.views.execute_tool")
     @patch("chat.views.stream_chat_completion")
     @patch("integrations.utils.auto_profile.update_auto_preference_profile")
@@ -1073,6 +1195,56 @@ class ChatViewSetSearchPlacesClarificationTests(APITransactionTestCase):
 
 
 class ChatViewSetToolExecutionFailureLoopTests(APITransactionTestCase):
+    @patch("chat.views.execute_tool")
+    @patch("chat.views.stream_chat_completion")
+    @patch("integrations.utils.auto_profile.update_auto_preference_profile")
+    def test_required_param_terminal_error_is_persisted_as_assistant_message(
+        self,
+        _mock_auto_profile,
+        mock_stream_chat_completion,
+        mock_execute_tool,
+    ):
+        user = User.objects.create_user(
+            username="chat-required-error-persist-user",
+            email="chat-required-error-persist-user@example.com",
+            password="password123",
+        )
+        self.client.force_authenticate(user=user)
+
+        conversation_response = self.client.post(
+            "/api/chat/conversations/",
+            {"title": "Required Error Persistence Test"},
+            format="json",
+        )
+        self.assertEqual(conversation_response.status_code, 201)
+        conversation_id = conversation_response.json()["id"]
+
+        async def validation_error_stream(*args, **kwargs):
+            yield 'data: {"tool_calls": [{"index": 0, "id": "call_move", "type": "function", "function": {"name": "move_itinerary_item", "arguments": "{}"}}]}\n\n'
+            yield "data: [DONE]\n\n"
+
+        mock_stream_chat_completion.side_effect = validation_error_stream
+        mock_execute_tool.return_value = {
+            "error": "collection_id, itinerary_item_id, and date are required"
+        }
+
+        response = self.client.post(
+            f"/api/chat/conversations/{conversation_id}/send_message/",
+            {"message": "Move that stop"},
+            format="json",
+        )
+
+        self.assertEqual(response.status_code, 200)
+        list(response.streaming_content)
+
+        conversation = user.chat_conversations.get(id=conversation_id)
+        self.assertTrue(
+            conversation.messages.filter(
+                role="assistant",
+                content__contains="attempted to call 'move_itinerary_item' without required arguments",
+            ).exists()
+        )
+
     @patch("chat.views.execute_tool")
     @patch("chat.views.stream_chat_completion")
     @patch("integrations.utils.auto_profile.update_auto_preference_profile")
@@ -1145,6 +1317,14 @@ class ChatViewSetToolExecutionFailureLoopTests(APITransactionTestCase):
         self.assertEqual(mock_stream_chat_completion.call_count, 3)
         self.assertEqual(mock_execute_tool.call_count, 3)
 
+        conversation = user.chat_conversations.get(id=conversation_id)
+        self.assertTrue(
+            conversation.messages.filter(
+                role="assistant",
+                content__contains="could not complete 'web_search'",
+            ).exists()
+        )
+
     @patch("chat.views.execute_tool")
     @patch("chat.views.stream_chat_completion")
     @patch("integrations.utils.auto_profile.update_auto_preference_profile")