diff --git a/flytekit/bin/entrypoint.py b/flytekit/bin/entrypoint.py
index 0970e2b6ab..90e54ad3b6 100644
--- a/flytekit/bin/entrypoint.py
+++ b/flytekit/bin/entrypoint.py
@@ -150,8 +150,9 @@ def _dispatch_execute(
 
             # Go over each output and create a separate offloaded in case its size is too large
             for k, v in outputs.literals.items():
+                literal_map_copy[k] = v
+
                 if not offloading_enabled:
-                    literal_map_copy[k] = v
                     continue
 
                 lit = v.to_flyte_idl()
diff --git a/tests/flytekit/unit/bin/test_python_entrypoint.py b/tests/flytekit/unit/bin/test_python_entrypoint.py
index 7e58799caf..b62bfd8e34 100644
--- a/tests/flytekit/unit/bin/test_python_entrypoint.py
+++ b/tests/flytekit/unit/bin/test_python_entrypoint.py
@@ -501,15 +501,7 @@ def t1(a: typing.List[int]) -> typing.List[str]:
         xs: typing.List[int] = [1, 2, 3]
         input_literal_map = _literal_models.LiteralMap(
             {
-                "a": _literal_models.Literal(
-                    collection=_literal_models.LiteralCollection(
-                        literals=[
-                            _literal_models.Literal(
-                                scalar=_literal_models.Scalar(primitive=_literal_models.Primitive(integer=x)),
-                            ) for x in xs
-                        ]
-                    )
-                )
+                "a": TypeEngine.to_literal(ctx, xs, typing.List[int], TypeEngine.to_literal_type(typing.List[int])),
             }
         )
 
@@ -527,7 +519,7 @@ def t1(a: typing.List[int]) -> typing.List[str]:
                         lit.ParseFromString(f.read())
                         assert len(lit.literals) == 1
                         assert "o0" in lit.literals
-                        assert lit.literals["o0"].offloaded_metadata is not None
+                        assert lit.literals["o0"].HasField("offloaded_metadata") == True
                         assert lit.literals["o0"].offloaded_metadata.size_bytes == 62
                         assert lit.literals["o0"].offloaded_metadata.uri.endswith("/o0_offloaded_metadata.pb")
                         assert lit.literals["o0"].offloaded_metadata.inferred_type == LiteralType(collection_type=LiteralType(simple=SimpleType.STRING)).to_flyte_idl()
@@ -592,12 +584,12 @@ def t1(xs: typing.List[int]) -> typing.Tuple[int, typing.List[str]]:
                         lit.ParseFromString(f.read())
                         assert len(lit.literals) == 2
                         assert "o0" in lit.literals
-                        assert lit.literals["o0"].offloaded_metadata is not None
+                        assert lit.literals["o0"].HasField("offloaded_metadata") == True
                         assert lit.literals["o0"].offloaded_metadata.size_bytes == 6
                         assert lit.literals["o0"].offloaded_metadata.uri.endswith("/o0_offloaded_metadata.pb")
                         assert lit.literals["o0"].offloaded_metadata.inferred_type == LiteralType(simple=SimpleType.INTEGER).to_flyte_idl()
                         assert "o1" in lit.literals
-                        assert lit.literals["o1"].offloaded_metadata is not None
+                        assert lit.literals["o1"].HasField("offloaded_metadata") == True
                         assert lit.literals["o1"].offloaded_metadata.size_bytes == 82
                         assert lit.literals["o1"].offloaded_metadata.uri.endswith("/o1_offloaded_metadata.pb")
                         assert lit.literals["o1"].offloaded_metadata.inferred_type == LiteralType(collection_type=LiteralType(simple=SimpleType.STRING)).to_flyte_idl()
@@ -749,3 +741,86 @@ def t1(n: int) -> typing.Annotated[A, HashMethod(lambda x: str(x.a))]:
                         assert a.a == 1234
                     else:
                         assert False, f"Unexpected file {ff}"
+
+
+def test_dispatch_execute_offloaded_nested_lists_of_literals(tmp_path_factory):
+    @task
+    def t1(a: typing.List[int]) -> typing.List[typing.List[str]]:
+        return [[f"string is: {x}" for x in a] for _ in range(len(a))]
+
+    inputs_path = tmp_path_factory.mktemp("inputs")
+    outputs_path = tmp_path_factory.mktemp("outputs")
+
+    ctx = context_manager.FlyteContext.current_context()
+    with get_flyte_context(tmp_path_factory, outputs_path) as ctx:
+        xs: typing.List[int] = [1, 2, 3]
+        input_literal_map = _literal_models.LiteralMap(
+            {
+                "a": TypeEngine.to_literal(ctx, xs, typing.List[int], TypeEngine.to_literal_type(typing.List[int])),
+            }
+        )
+
+        write_proto_to_file(input_literal_map.to_flyte_idl(), str(inputs_path/"inputs.pb"))
+
+        with mock.patch.dict(os.environ, {"_F_L_MIN_SIZE_MB": "0"}):
+            _dispatch_execute(ctx, lambda: t1, str(inputs_path/"inputs.pb"), str(outputs_path.absolute()))
+
+            assert "error.pb" not in os.listdir(outputs_path)
+
+            for ff in os.listdir(outputs_path):
+                with open(outputs_path/ff, "rb") as f:
+                    if ff == "outputs.pb":
+                        lit = literals_pb2.LiteralMap()
+                        lit.ParseFromString(f.read())
+                        assert len(lit.literals) == 1
+                        assert "o0" in lit.literals
+                        assert lit.literals["o0"].HasField("offloaded_metadata") == True
+                        assert lit.literals["o0"].offloaded_metadata.size_bytes == 195
+                        assert lit.literals["o0"].offloaded_metadata.uri.endswith("/o0_offloaded_metadata.pb")
+                        assert lit.literals["o0"].offloaded_metadata.inferred_type == LiteralType(collection_type=LiteralType(collection_type=LiteralType(simple=SimpleType.STRING))).to_flyte_idl()
+                    elif ff == "o0_offloaded_metadata.pb":
+                        lit = literals_pb2.Literal()
+                        lit.ParseFromString(f.read())
+                        expected_output = [[f"string is: {x}" for x in xs] for _ in range(len(xs))]
+                        assert lit == TypeEngine.to_literal(ctx, expected_output, typing.List[typing.List[str]], TypeEngine.to_literal_type(typing.List[typing.List[str]])).to_flyte_idl()
+                    else:
+                        assert False, f"Unexpected file {ff}"
+
+
+def test_dispatch_execute_offloaded_nested_lists_of_literals_offloading_disabled(tmp_path_factory):
+    @task
+    def t1(a: typing.List[int]) -> typing.List[typing.List[str]]:
+        return [[f"string is: {x}" for x in a] for _ in range(len(a))]
+
+    inputs_path = tmp_path_factory.mktemp("inputs")
+    outputs_path = tmp_path_factory.mktemp("outputs")
+
+    ctx = context_manager.FlyteContext.current_context()
+    with get_flyte_context(tmp_path_factory, outputs_path) as ctx:
+        xs: typing.List[int] = [1, 2, 3]
+        input_literal_map = _literal_models.LiteralMap(
+            {
+                "a": TypeEngine.to_literal(ctx, xs, typing.List[int], TypeEngine.to_literal_type(typing.List[int])),
+            }
+        )
+
+        write_proto_to_file(input_literal_map.to_flyte_idl(), str(inputs_path/"inputs.pb"))
+
+        # Ensure that this is not set by an external source
+        assert os.environ.get("_F_L_MIN_SIZE_MB") is None
+
+        # Notice how we're setting the env var to None, which disables offloading completely
+        _dispatch_execute(ctx, lambda: t1, str(inputs_path/"inputs.pb"), str(outputs_path.absolute()))
+
+        assert "error.pb" not in os.listdir(outputs_path)
+
+        for ff in os.listdir(outputs_path):
+            with open(outputs_path/ff, "rb") as f:
+                if ff == "outputs.pb":
+                    lit = literals_pb2.LiteralMap()
+                    lit.ParseFromString(f.read())
+                    assert len(lit.literals) == 1
+                    assert "o0" in lit.literals
+                    assert lit.literals["o0"].HasField("offloaded_metadata") == False
+                else:
+                    assert False, f"Unexpected file {ff}"