diff --git a/Lib/annotationlib.py b/Lib/annotationlib.py
index 971f636f9714d7..b4cecb41d13c46 100644
--- a/Lib/annotationlib.py
+++ b/Lib/annotationlib.py
@@ -392,12 +392,19 @@ def binop(self, other):
     __mod__ = _make_binop(ast.Mod())
     __lshift__ = _make_binop(ast.LShift())
     __rshift__ = _make_binop(ast.RShift())
-    __or__ = _make_binop(ast.BitOr())
     __xor__ = _make_binop(ast.BitXor())
     __and__ = _make_binop(ast.BitAnd())
     __floordiv__ = _make_binop(ast.FloorDiv())
     __pow__ = _make_binop(ast.Pow())
 
+    def __or__(self, other):
+        if self.__stringifier_dict__.create_unions:
+            return types.UnionType[self, other]
+
+        return self.__make_new(
+            ast.BinOp(self.__get_ast(), ast.BitOr(), self.__convert_to_ast(other))
+        )
+
     del _make_binop
 
     def _make_rbinop(op: ast.AST):
@@ -416,12 +423,19 @@ def rbinop(self, other):
     __rmod__ = _make_rbinop(ast.Mod())
     __rlshift__ = _make_rbinop(ast.LShift())
     __rrshift__ = _make_rbinop(ast.RShift())
-    __ror__ = _make_rbinop(ast.BitOr())
     __rxor__ = _make_rbinop(ast.BitXor())
     __rand__ = _make_rbinop(ast.BitAnd())
     __rfloordiv__ = _make_rbinop(ast.FloorDiv())
     __rpow__ = _make_rbinop(ast.Pow())
 
+    def __ror__(self, other):
+        if self.__stringifier_dict__.create_unions:
+            return types.UnionType[other, self]
+
+        return self.__make_new(
+            ast.BinOp(self.__convert_to_ast(other), ast.BitOr(), self.__get_ast())
+        )
+
     del _make_rbinop
 
     def _make_compare(op):
@@ -459,12 +473,13 @@ def unary_op(self):
 
 
 class _StringifierDict(dict):
-    def __init__(self, namespace, globals=None, owner=None, is_class=False):
+    def __init__(self, namespace, globals=None, owner=None, is_class=False, create_unions=False):
         super().__init__(namespace)
         self.namespace = namespace
         self.globals = globals
         self.owner = owner
         self.is_class = is_class
+        self.create_unions = create_unions
         self.stringifiers = []
 
     def __missing__(self, key):
@@ -569,7 +584,13 @@ def call_annotate_function(annotate, format, *, owner=None, _is_evaluate=False):
         # that returns a bool and an defined set of attributes.
         namespace = {**annotate.__builtins__, **annotate.__globals__}
         is_class = isinstance(owner, type)
-        globals = _StringifierDict(namespace, annotate.__globals__, owner, is_class)
+        globals = _StringifierDict(
+            namespace,
+            annotate.__globals__,
+            owner,
+            is_class,
+            create_unions=True
+        )
         if annotate.__closure__:
             freevars = annotate.__code__.co_freevars
             new_closure = []
diff --git a/Lib/test/test_annotationlib.py b/Lib/test/test_annotationlib.py
index 0890be529a7e52..6f17c85659c34e 100644
--- a/Lib/test/test_annotationlib.py
+++ b/Lib/test/test_annotationlib.py
@@ -115,8 +115,11 @@ def f(
         self.assertEqual(z_anno, support.EqualToForwardRef("some(module)", owner=f))
 
         alpha_anno = anno["alpha"]
-        self.assertIsInstance(alpha_anno, ForwardRef)
-        self.assertEqual(alpha_anno, support.EqualToForwardRef("some | obj", owner=f))
+        self.assertIsInstance(alpha_anno, Union)
+        self.assertEqual(
+            typing.get_args(alpha_anno),
+            (support.EqualToForwardRef("some", owner=f), support.EqualToForwardRef("obj", owner=f))
+        )
 
         beta_anno = anno["beta"]
         self.assertIsInstance(beta_anno, ForwardRef)
@@ -126,6 +129,27 @@ def f(
         self.assertIsInstance(gamma_anno, ForwardRef)
         self.assertEqual(gamma_anno, support.EqualToForwardRef("some < obj", owner=f))
 
+    def test_partially_nonexistent_union(self):
+        # Test unions with '|' syntax equal unions with typing.Union[] with some forwardrefs
+        class UnionForwardrefs:
+            pipe: str | undefined
+            union: Union[str, undefined]
+
+        annos = get_annotations(UnionForwardrefs, format=Format.FORWARDREF)
+
+        match = (
+            str,
+            support.EqualToForwardRef("undefined", is_class=True, owner=UnionForwardrefs)
+        )
+
+        self.assertEqual(
+            typing.get_args(annos["pipe"]),
+            typing.get_args(annos["union"])
+        )
+
+        self.assertEqual(typing.get_args(annos["pipe"]), match)
+        self.assertEqual(typing.get_args(annos["union"]), match)
+
 
 class TestSourceFormat(unittest.TestCase):
     def test_closure(self):