diff --git a/flytekit/core/type_engine.py b/flytekit/core/type_engine.py
index d76a9c3da1..157b1a6a1d 100644
--- a/flytekit/core/type_engine.py
+++ b/flytekit/core/type_engine.py
@@ -988,8 +988,11 @@ def to_literal(self, ctx: FlyteContext, python_val: T, python_type: Type[T], exp
         if ListTransformer.is_batchable(python_type):
             batchSize = len(python_val)  # default batch size
             # parse annotated to get the number of items saved in a pickle file.
-            if get_origin(python_type) is Annotated and type(get_args(python_type)[1]) == int:
-                batchSize = get_args(python_type)[1]
+            if get_origin(python_type) is Annotated:
+                for annotation in get_args(python_type)[1:]:
+                    if isinstance(annotation, int):
+                        batchSize = annotation
+                        break
             lit_list = [TypeEngine.to_literal(ctx, python_val[i : i + batchSize], FlytePickle, expected.collection_type) for i in range(0, len(python_val), batchSize)]  # type: ignore
         else:
             t = self.get_sub_type(python_type)
diff --git a/tests/flytekit/unit/core/test_type_engine.py b/tests/flytekit/unit/core/test_type_engine.py
index d87493eb05..f04b61651d 100644
--- a/tests/flytekit/unit/core/test_type_engine.py
+++ b/tests/flytekit/unit/core/test_type_engine.py
@@ -18,7 +18,7 @@
 from marshmallow_enum import LoadDumpOptions
 from marshmallow_jsonschema import JSONSchema
 from pandas._testing import assert_frame_equal
-from typing_extensions import Annotated, get_args, get_origin
+from typing_extensions import Annotated
 
 from flytekit import kwtypes
 from flytekit.core.annotation import FlyteAnnotation
@@ -1576,27 +1576,22 @@ def test_file_ext_with_flyte_file_wrong_type():
     assert str(e.value) == "Underlying type of File Extension must be of type <str>"
 
 
-def test_batch_pickle_list():
+@pytest.mark.parametrize(
+    "python_val, python_type, batch_size",
+    [
+        ([{"a": {0: "foo"}}] * 5, typing.List[typing.Dict[str, FlytePickle]], 5),
+        ([{"a": {0: "foo"}}] * 5, Annotated[typing.List[typing.Dict[str, FlytePickle]], 2], 2),
+        ([{"a": {0: "foo"}}] * 6, Annotated[typing.List[typing.Dict[str, FlytePickle]], HashMethod(function=str), 2], 2),
+    ],
+)
+def test_batch_pickle_list(python_val, python_type, batch_size):
     from math import ceil
 
-    python_val = [{"a": {0: "foo"}}] * 5
-    python_type_list = [
-        typing.List[typing.Dict[str, FlytePickle]],
-        Annotated[typing.List[typing.Dict[str, FlytePickle]], 2],
-    ]
-
-    for python_type in python_type_list:
-        batch_size = len(python_val)
-        if get_origin(python_type) is Annotated:
-            batch_size = get_args(python_type)[1]
-
-        ctx = FlyteContext.current_context()
-        expected = TypeEngine.to_literal_type(python_type)
-
-        lv = TypeEngine.to_literal(ctx, python_val, python_type, expected)
-        # For example, if the batch size is 2 and the length of the list is 5, the list should be split into ceil(5/3) = 3 chunks.
-        # By default, the batch_size is set to the length of the whole list.
-        assert len(lv.collection.literals) == ceil(len(python_val) / batch_size)
-
-        pv = TypeEngine.to_python_value(ctx, lv, python_type)
-        assert pv == python_val
+    ctx = FlyteContext.current_context()
+    expected = TypeEngine.to_literal_type(python_type)
+    lv = TypeEngine.to_literal(ctx, python_val, python_type, expected)
+    # For example, if the batch size is 2 and the length of the list is 5, the list should be split into ceil(5/3) = 3 chunks.
+    # By default, the batch_size is set to the length of the whole list.
+    assert len(lv.collection.literals) == ceil(len(python_val) / batch_size)
+    pv = TypeEngine.to_python_value(ctx, lv, python_type)
+    assert pv == python_val