diff --git a/guardrails/schema/json_schema.py b/guardrails/schema/json_schema.py
index f555925f2..07c1c1a33 100644
--- a/guardrails/schema/json_schema.py
+++ b/guardrails/schema/json_schema.py
@@ -453,7 +453,7 @@ async def async_validate(
 
         return validated_response
 
-    def introspect(self, data: Any) -> Tuple[List[ReAsk], Optional[Dict]]:
+    def introspect(self, data: Any) -> Tuple[List[ReAsk], Union[Dict, List, None]]:
         if isinstance(data, SkeletonReAsk):
             return [data], None
         elif isinstance(data, NonParseableReAsk):
diff --git a/guardrails/utils/reask_utils.py b/guardrails/utils/reask_utils.py
index d6a1a4faf..926eb7fd4 100644
--- a/guardrails/utils/reask_utils.py
+++ b/guardrails/utils/reask_utils.py
@@ -26,8 +26,8 @@ class NonParseableReAsk(ReAsk):
 
 
 def gather_reasks(
-    validated_output: Optional[Union[str, Dict, ReAsk]]
-) -> Tuple[List[ReAsk], Optional[Dict]]:
+    validated_output: Optional[Union[str, Dict, List, ReAsk]]
+) -> Tuple[List[ReAsk], Union[Dict, List, None]]:
     """Traverse output and gather all ReAsk objects.
 
     Args: