diff --git a/flytekit/core/type_engine.py b/flytekit/core/type_engine.py
index 9c48908f98..7b4f17eda5 100644
--- a/flytekit/core/type_engine.py
+++ b/flytekit/core/type_engine.py
@@ -1141,7 +1141,12 @@ def to_python_value(self, ctx: FlyteContext, lv: Literal, expected_python_type:
         try:
             lits = lv.collection.literals
         except AttributeError:
-            raise TypeTransformerFailedError()
+            raise TypeTransformerFailedError(
+                (
+                    f"The expected python type is '{expected_python_type}' but the received Flyte literal value "
+                    f"is not a collection (Flyte's representation of Python lists)."
+                )
+            )
         if self.is_batchable(expected_python_type):
             from flytekit.types.pickle import FlytePickle