diff --git a/flytekit/core/type_engine.py b/flytekit/core/type_engine.py
index e7ca650c49..34444cd1b4 100644
--- a/flytekit/core/type_engine.py
+++ b/flytekit/core/type_engine.py
@@ -1540,6 +1540,9 @@ def assert_type(self, t: Type[T], v: T):
         python_type = get_underlying_type(t)
         if _is_union_type(python_type):
             for sub_type in get_args(python_type):
+                if sub_type == typing.Any:
+                    # this is an edge case
+                    return
                 try:
                     super().assert_type(sub_type, v)
                     return