diff --git a/backend/alembic/versions/b082fec533f0_make_last_attempt_status_nullable.py b/backend/alembic/versions/b082fec533f0_make_last_attempt_status_nullable.py
index a6938e365c6..db7b330c3e0 100644
--- a/backend/alembic/versions/b082fec533f0_make_last_attempt_status_nullable.py
+++ b/backend/alembic/versions/b082fec533f0_make_last_attempt_status_nullable.py
@@ -31,6 +31,12 @@ def upgrade() -> None:
 
 
 def downgrade() -> None:
+    # First, update any null values to a default value
+    op.execute(
+        "UPDATE connector_credential_pair SET last_attempt_status = 'NOT_STARTED' WHERE last_attempt_status IS NULL"
+    )
+
+    # Then, make the column non-nullable
     op.alter_column(
         "connector_credential_pair",
         "last_attempt_status",
diff --git a/backend/danswer/llm/answering/answer.py b/backend/danswer/llm/answering/answer.py
index 4648e0fe821..d2aeb1b14c4 100644
--- a/backend/danswer/llm/answering/answer.py
+++ b/backend/danswer/llm/answering/answer.py
@@ -237,6 +237,7 @@ def _raw_output_for_explicit_tool_calling_llms(
                 prompt=prompt,
                 tools=final_tool_definitions if final_tool_definitions else None,
                 tool_choice="required" if self.force_use_tool.force_use else None,
+                structured_response_format=self.answer_style_config.structured_response_format,
             ):
                 if isinstance(message, AIMessageChunk) and (
                     message.tool_call_chunks or message.tool_calls
@@ -331,7 +332,10 @@ def _process_llm_stream(
         tool_choice: ToolChoiceOptions | None = None,
     ) -> Iterator[str | StreamStopInfo]:
         for message in self.llm.stream(
-            prompt=prompt, tools=tools, tool_choice=tool_choice
+            prompt=prompt,
+            tools=tools,
+            tool_choice=tool_choice,
+            structured_response_format=self.answer_style_config.structured_response_format,
         ):
             if isinstance(message, AIMessageChunk):
                 if message.content:
diff --git a/backend/danswer/redis/redis_pool.py b/backend/danswer/redis/redis_pool.py
index 3f2ec03d77f..0fe5c0ddd42 100644
--- a/backend/danswer/redis/redis_pool.py
+++ b/backend/danswer/redis/redis_pool.py
@@ -102,6 +102,9 @@ def __getattribute__(self, item: str) -> Any:
             "reacquire",
             "create_lock",
             "startswith",
+            "sadd",
+            "srem",
+            "scard",
         ]  # Regular methods that need simple prefixing
 
         if item == "scan_iter":
diff --git a/backend/tests/integration/tests/dev_apis/test_simple_chat_api.py b/backend/tests/integration/tests/dev_apis/test_simple_chat_api.py
index fd7db7098bd..c37d1a6235d 100644
--- a/backend/tests/integration/tests/dev_apis/test_simple_chat_api.py
+++ b/backend/tests/integration/tests/dev_apis/test_simple_chat_api.py
@@ -154,42 +154,38 @@ def test_send_message_simple_with_history_strict_json(
     new_admin_user: DATestUser | None,
 ) -> None:
     # create connectors
-    cc_pair_1: DATestCCPair = CCPairManager.create_from_scratch(
-        user_performing_action=new_admin_user,
-    )
-    api_key: DATestAPIKey = APIKeyManager.create(
-        user_performing_action=new_admin_user,
-    )
     LLMProviderManager.create(user_performing_action=new_admin_user)
-    cc_pair_1.documents = DocumentManager.seed_dummy_docs(
-        cc_pair=cc_pair_1,
-        num_docs=NUM_DOCS,
-        api_key=api_key,
-    )
 
     response = requests.post(
         f"{API_SERVER_URL}/chat/send-message-simple-with-history",
         json={
+            # intentionally not relevant prompt to ensure that the
+            # structured response format is actually used
             "messages": [
                 {
-                    "message": "List the names of the first three US presidents in JSON format",
+                    "message": "What is green?",
                     "role": MessageType.USER.value,
                 }
             ],
             "persona_id": 0,
             "prompt_id": 0,
             "structured_response_format": {
-                "type": "json_object",
-                "schema": {
-                    "type": "object",
-                    "properties": {
-                        "presidents": {
-                            "type": "array",
-                            "items": {"type": "string"},
-                            "description": "List of the first three US presidents",
-                        }
+                "type": "json_schema",
+                "json_schema": {
+                    "name": "presidents",
+                    "schema": {
+                        "type": "object",
+                        "properties": {
+                            "presidents": {
+                                "type": "array",
+                                "items": {"type": "string"},
+                                "description": "List of the first three US presidents",
+                            }
+                        },
+                        "required": ["presidents"],
+                        "additionalProperties": False,
                     },
-                    "required": ["presidents"],
+                    "strict": True,
                 },
             },
         },
@@ -211,14 +207,17 @@ def clean_json_string(json_string: str) -> str:
     try:
         clean_answer = clean_json_string(response_json["answer"])
         parsed_answer = json.loads(clean_answer)
+
+        # NOTE: do not check content, just the structure
         assert isinstance(parsed_answer, dict)
         assert "presidents" in parsed_answer
         assert isinstance(parsed_answer["presidents"], list)
-        assert len(parsed_answer["presidents"]) == 3
         for president in parsed_answer["presidents"]:
             assert isinstance(president, str)
     except json.JSONDecodeError:
-        assert False, "The answer is not a valid JSON object"
+        assert (
+            False
+        ), f"The answer is not a valid JSON object - '{response_json['answer']}'"
 
     # Check that the answer_citationless is also valid JSON
     assert "answer_citationless" in response_json