diff --git a/flytekit/core/promise.py b/flytekit/core/promise.py
index 220fc3fb89..ba326ec27e 100644
--- a/flytekit/core/promise.py
+++ b/flytekit/core/promise.py
@@ -697,6 +697,15 @@ def binding_data_from_python_std(
         )
 
     elif t_value is not None and expected_literal_type.union_type is not None:
+        # If the value is not a container type, then we can directly convert it to a scalar in the Union case.
+        # This pushes the handling of the Union types to the type engine.
+        if not isinstance(t_value, list) and not isinstance(t_value, dict):
+            scalar = TypeEngine.to_literal(ctx, t_value, t_value_type or type(t_value), expected_literal_type).scalar
+            return _literals_models.BindingData(scalar=scalar)
+
+        # If it is a container type, then we need to iterate over the variants in the Union type, try each one. This is
+        # akin to what the Type Engine does when it finds a Union type (see the UnionTransformer), but we can't rely on
+        # that in this case, because of the mix and match of realized values, and Promises.
         for i in range(len(expected_literal_type.union_type.variants)):
             try:
                 lt_type = expected_literal_type.union_type.variants[i]
diff --git a/tests/flytekit/unit/core/test_promise.py b/tests/flytekit/unit/core/test_promise.py
index 74f3db99e3..e022c875e0 100644
--- a/tests/flytekit/unit/core/test_promise.py
+++ b/tests/flytekit/unit/core/test_promise.py
@@ -13,6 +13,7 @@
 from flytekit.core.promise import (
     Promise,
     VoidPromise,
+    binding_data_from_python_std,
     create_and_link_node,
     create_and_link_node_from_remote,
     resolve_attr_path_in_promise,
@@ -20,6 +21,7 @@
 )
 from flytekit.core.type_engine import TypeEngine
 from flytekit.exceptions.user import FlyteAssertion, FlytePromiseAttributeResolveException
+from flytekit.models.types import LiteralType, SimpleType, TypeStructure
 from flytekit.types.pickle.pickle import BatchSize
 
 
@@ -234,3 +236,18 @@ class Foo:
     # exception
     with pytest.raises(FlytePromiseAttributeResolveException):
         tgt_promise = resolve_attr_path_in_promise(src_promise["c"])
+
+
+def test_prom_with_union_literals():
+    ctx = FlyteContextManager.current_context()
+    pt = typing.Union[str, int]
+    lt = TypeEngine.to_literal_type(pt)
+    assert lt.union_type.variants == [
+        LiteralType(simple=SimpleType.STRING, structure=TypeStructure(tag="str")),
+        LiteralType(simple=SimpleType.INTEGER, structure=TypeStructure(tag="int")),
+    ]
+
+    bd = binding_data_from_python_std(ctx, lt, 3, pt, [])
+    assert bd.scalar.union.stored_type.structure.tag == "int"
+    bd = binding_data_from_python_std(ctx, lt, "hello", pt, [])
+    assert bd.scalar.union.stored_type.structure.tag == "str"
diff --git a/tests/flytekit/unit/core/test_type_engine.py b/tests/flytekit/unit/core/test_type_engine.py
index d4db4f34fe..0546b9dc7a 100644
--- a/tests/flytekit/unit/core/test_type_engine.py
+++ b/tests/flytekit/unit/core/test_type_engine.py
@@ -1759,6 +1759,42 @@ def test_annotated_union_type():
     assert v == "hello"
 
 
+def test_union_type_simple():
+    pt = typing.Union[str, int]
+    lt = TypeEngine.to_literal_type(pt)
+    assert lt.union_type.variants == [
+        LiteralType(simple=SimpleType.STRING, structure=TypeStructure(tag="str")),
+        LiteralType(simple=SimpleType.INTEGER, structure=TypeStructure(tag="int")),
+    ]
+    ctx = FlyteContextManager.current_context()
+    lv = TypeEngine.to_literal(ctx, 3, pt, lt)
+    assert lv.scalar.union is not None
+    assert lv.scalar.union.stored_type.structure.tag == "int"
+    assert lv.scalar.union.stored_type.structure.dataclass_type is None
+
+
+def test_union_containers():
+    pt = typing.Union[typing.List[typing.Dict[str, typing.List[int]]], typing.Dict[str, typing.List[int]], int]
+    lt = TypeEngine.to_literal_type(pt)
+
+    list_of_maps_of_list_ints = [
+        {"first_map_a": [42], "first_map_b": [42, 2]},
+        {
+            "second_map_c": [33],
+            "second_map_d": [9, 99],
+        },
+    ]
+    map_of_list_ints = {
+        "ll_1": [1, 23, 3],
+        "ll_2": [4, 5, 6],
+    }
+    ctx = FlyteContextManager.current_context()
+    lv = TypeEngine.to_literal(ctx, list_of_maps_of_list_ints, pt, lt)
+    assert lv.scalar.union.stored_type.structure.tag == "Typed List"
+    lv = TypeEngine.to_literal(ctx, map_of_list_ints, pt, lt)
+    assert lv.scalar.union.stored_type.structure.tag == "Python Dictionary"
+
+
 @pytest.mark.skipif(sys.version_info < (3, 10), reason="PEP604 requires >=3.10.")
 def test_optional_type():
     pt = typing.Optional[int]