From 87e8de68453b64be000062e159be0bbbe521c597 Mon Sep 17 00:00:00 2001
From: STerliakov <terlya.stas@gmail.com>
Date: Mon, 7 Apr 2025 21:25:30 +0200
Subject: [PATCH] Flatten union before contracting literals when checking
 subtyping

---
 mypy/subtypes.py                  |  5 ++++-
 mypy/typeops.py                   |  2 ++
 test-data/unit/check-literal.test | 22 ++++++++++++++++++++++
 3 files changed, 28 insertions(+), 1 deletion(-)

diff --git a/mypy/subtypes.py b/mypy/subtypes.py
index 41bb4601e23f..71b8b0ba59f5 100644
--- a/mypy/subtypes.py
+++ b/mypy/subtypes.py
@@ -67,6 +67,7 @@
     UnionType,
     UnpackType,
     find_unpack_in_list,
+    flatten_nested_unions,
     get_proper_type,
     is_named_instance,
     split_with_prefix_and_suffix,
@@ -327,7 +328,9 @@ def _is_subtype(
             and isinstance(left, Instance)
             and (left.type.is_enum or left.type.fullname == "builtins.bool")
         ):
-            right = UnionType(mypy.typeops.try_contracting_literals_in_union(right.items))
+            right = UnionType(
+                mypy.typeops.try_contracting_literals_in_union(flatten_nested_unions(right.items))
+            )
             if proper_subtype:
                 is_subtype_of_item = any(
                     is_proper_subtype(orig_left, item, subtype_context=subtype_context)
diff --git a/mypy/typeops.py b/mypy/typeops.py
index 06ecc0fb3fda..bcf946900563 100644
--- a/mypy/typeops.py
+++ b/mypy/typeops.py
@@ -1069,6 +1069,8 @@ class Status(Enum):
 def try_contracting_literals_in_union(types: Sequence[Type]) -> list[ProperType]:
     """Contracts any literal types back into a sum type if possible.
 
+    Requires a flattened union and does not descend into children.
+
     Will replace the first instance of the literal with the sum type and
     remove all others.
 
diff --git a/test-data/unit/check-literal.test b/test-data/unit/check-literal.test
index 88c02f70488c..f36eff28f33f 100644
--- a/test-data/unit/check-literal.test
+++ b/test-data/unit/check-literal.test
@@ -2765,6 +2765,28 @@ reveal_type(x)  # N: Revealed type is "Literal[__main__.Foo.A]"
 reveal_type(y)  # N: Revealed type is "Literal[__main__.Foo.A]"
 [builtins fixtures/tuple.pyi]
 
+[case testLiteralUnionEnumAliasAssignable]
+from enum import Enum
+from typing import Literal, Union
+
+class E(Enum):
+    A = 'a'
+    B = 'b'
+    C = 'c'
+
+A = Literal[E.A]
+B = Literal[E.B, E.C]
+
+def f(x: Union[A, B]) -> None: ...
+def f2(x: Union[A, Literal[E.B, E.C]]) -> None: ...
+def f3(x: Union[Literal[E.A], B]) -> None: ...
+
+def main(x: E) -> None:
+    f(x)
+    f2(x)
+    f3(x)
+[builtins fixtures/tuple.pyi]
+
 [case testStrictEqualityLiteralTrueVsFalse]
 # mypy: strict-equality