diff --git a/guardrails/classes/output_type.py b/guardrails/classes/output_type.py
index f40714047..2aff9fc82 100644
--- a/guardrails/classes/output_type.py
+++ b/guardrails/classes/output_type.py
@@ -1,3 +1,3 @@
 from typing import Dict, List, TypeVar
 
-OT = TypeVar("OT", str, Dict, List)
+OT = TypeVar("OT", str, List, Dict)
diff --git a/guardrails/classes/validation_outcome.py b/guardrails/classes/validation_outcome.py
index 4a7586e8b..4f9df16ae 100644
--- a/guardrails/classes/validation_outcome.py
+++ b/guardrails/classes/validation_outcome.py
@@ -1,6 +1,7 @@
 from typing import Generic, Iterator, Optional, Tuple, Union, cast
 
 from pydantic import Field
+from rich.pretty import pretty_repr
 
 from guardrails.classes.history import Call, Iteration
 from guardrails.classes.output_type import OT
@@ -83,3 +84,6 @@ def __iter__(
     def __getitem__(self, keys):
         """Get a subset of the ValidationOutcome's fields."""
         return iter(getattr(self, k) for k in keys)
+
+    def __str__(self) -> str:
+        return pretty_repr(self)
diff --git a/guardrails/utils/reask_utils.py b/guardrails/utils/reask_utils.py
index c42aba16c..d6a1a4faf 100644
--- a/guardrails/utils/reask_utils.py
+++ b/guardrails/utils/reask_utils.py
@@ -82,6 +82,10 @@ def _gather_reasks_in_list(
         valid_output = deepcopy(validated_output)
         _gather_reasks_in_dict(validated_output, valid_output)
         return reasks, valid_output
+    elif isinstance(validated_output, List):
+        valid_output = deepcopy(validated_output)
+        _gather_reasks_in_list(validated_output, valid_output)
+        return reasks, valid_output
     return reasks, None