diff --git a/flytekit/core/type_engine.py b/flytekit/core/type_engine.py
index be5cbc6255..34444cd1b4 100644
--- a/flytekit/core/type_engine.py
+++ b/flytekit/core/type_engine.py
@@ -148,7 +148,37 @@ def type_assertions_enabled(self) -> bool:
         """
         return self._type_assertions_enabled
 
+    def isinstance_generic(self, obj, generic_alias):
+        origin = get_origin(generic_alias)  # list from list[int])
+        args = get_args(generic_alias)  # (int,) from list[int]
+
+        if not isinstance(obj, origin):
+            raise TypeTransformerFailedError(f"Value '{obj}' is not of container type {origin}")
+
+        # Optionally check the type of elements if it's a collection like list or dict
+        if origin in {list, tuple, set}:
+            for item in obj:
+                self.assert_type(args[0], item)
+                return
+            raise TypeTransformerFailedError(f"Not all items in '{obj}' are of type {args[0]}")
+
+        if origin is dict:
+            key_type, value_type = args
+            for k, v in obj.items():
+                self.assert_type(key_type, k)
+                self.assert_type(value_type, v)
+                return
+            raise TypeTransformerFailedError(f"Not all values in '{obj}' are of type {value_type}")
+
+        return
+
     def assert_type(self, t: Type[T], v: T):
+        if sys.version_info >= (3, 10):
+            import types
+
+            if isinstance(t, types.GenericAlias):
+                return self.isinstance_generic(v, t)
+
         if not hasattr(t, "__origin__") and not isinstance(v, t):
             raise TypeTransformerFailedError(f"Expected value of type {t} but got '{v}' of type {type(v)}")
 
@@ -1506,6 +1536,22 @@ def get_sub_type_in_optional(t: Type[T]) -> Type[T]:
         """
         return get_args(t)[0]
 
+    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
+                except TypeTransformerFailedError:
+                    continue
+            raise TypeTransformerFailedError(f"Value {v} is not of type {t}")
+        else:
+            super().assert_type(t, v)
+
     def get_literal_type(self, t: Type[T]) -> Optional[LiteralType]:
         t = get_underlying_type(t)
 
diff --git a/tests/flytekit/unit/core/test_type_engine.py b/tests/flytekit/unit/core/test_type_engine.py
index 57f6cddecf..eb4c0d0f44 100644
--- a/tests/flytekit/unit/core/test_type_engine.py
+++ b/tests/flytekit/unit/core/test_type_engine.py
@@ -3275,3 +3275,40 @@ def run():
         assert mock_wrapper.mock_calls[-N:] == [mock.call.after_import_mock()]*N
         expected_number_of_register_calls = len(mock_wrapper.mock_calls) - N
         assert all([mock_call[0] == "mock_register" for mock_call in mock_wrapper.mock_calls[:expected_number_of_register_calls]])
+
+
+@pytest.mark.skipif(sys.version_info < (3, 10), reason="PEP604 requires >=3.10, 585 requires >=3.9")
+def test_option_list_with_pipe():
+    pt = list[int] | None
+    lt = TypeEngine.to_literal_type(pt)
+
+    ctx = FlyteContextManager.current_context()
+    lit = TypeEngine.to_literal(ctx, [1, 2, 3], pt, lt)
+    assert lit.scalar.union.value.collection.literals[2].scalar.primitive.integer == 3
+
+    TypeEngine.to_literal(ctx, None, pt, lt)
+
+    with pytest.raises(TypeTransformerFailedError):
+        TypeEngine.to_literal(ctx, [1, 2, "3"], pt, lt)
+
+
+@pytest.mark.skipif(sys.version_info < (3, 10), reason="PEP604 requires >=3.10, 585 requires >=3.9")
+def test_option_list_with_pipe_2():
+    pt = list[list[dict[str, str]] | None] | None
+    lt = TypeEngine.to_literal_type(pt)
+
+    ctx = FlyteContextManager.current_context()
+    lit = TypeEngine.to_literal(ctx, [[{"a": "one"}], None, [{"b": "two"}]], pt, lt)
+    uv = lit.scalar.union.value
+    assert uv is not None
+    assert len(uv.collection.literals) == 3
+    first = uv.collection.literals[0]
+    assert first.scalar.union.value.collection.literals[0].map.literals["a"].scalar.primitive.string_value == "one"
+
+    assert len(lt.union_type.variants) == 2
+    v1 = lt.union_type.variants[0]
+    assert len(v1.collection_type.union_type.variants) == 2
+    assert v1.collection_type.union_type.variants[0].collection_type.map_value_type.simple == SimpleType.STRING
+
+    with pytest.raises(TypeTransformerFailedError):
+        TypeEngine.to_literal(ctx, [[{"a": "one"}], None, [{"b": 3}]], pt, lt)