diff --git a/packages/pyright-internal/src/analyzer/typeGuards.ts b/packages/pyright-internal/src/analyzer/typeGuards.ts
index 05f881cb9..364d37623 100644
--- a/packages/pyright-internal/src/analyzer/typeGuards.ts
+++ b/packages/pyright-internal/src/analyzer/typeGuards.ts
@@ -2543,7 +2543,8 @@ function narrowTypeForLiteralComparison(
             }
         } else if (isPositiveTest) {
             if (isIsOperator || isNoneInstance(subtype)) {
-                return undefined;
+                const isSubtype = evaluator.assignType(subtype, literalType);
+                return isSubtype ? literalType : undefined;
             }
         }
 
diff --git a/packages/pyright-internal/src/tests/samples/typeNarrowingEnum2.py b/packages/pyright-internal/src/tests/samples/typeNarrowingEnum2.py
index ff241d50c..597af89cc 100644
--- a/packages/pyright-internal/src/tests/samples/typeNarrowingEnum2.py
+++ b/packages/pyright-internal/src/tests/samples/typeNarrowingEnum2.py
@@ -11,8 +11,7 @@ class SomeEnum(Enum):
     VALUE2 = 2
 
 
-def assert_never(val: NoReturn):
-    ...
+def assert_never(val: NoReturn): ...
 
 
 def func1(a: SomeEnum):
@@ -69,3 +68,10 @@ def func7(a: Union[str, bool]) -> str:
     elif a is True:
         return "True"
     return a
+
+
+def func8(a: object):
+    if a is SomeEnum.VALUE1 or a is SomeEnum.VALUE2:
+        reveal_type(a, expected_text="Literal[SomeEnum.VALUE1, SomeEnum.VALUE2]")
+    else:
+        reveal_type(a, expected_text="object")