python
diff --git a/‎mypy/checker.py
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diff --git a/‎test-data/unit/check-literal.test
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diff --git a/‎test-data/unit/fixtures/primitives.pyi
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@@ -4372,7 +4372,7 @@ def check_simple_assignment(
             if (
                 isinstance(get_proper_type(lvalue_type), UnionType)
                 # Skip literal types, as they have special logic (for better errors).
-                and not isinstance(get_proper_type(rvalue_type), LiteralType)
+                and not is_literal_type_like(rvalue_type)
                 and not self.simple_rvalue(rvalue)
             ):
                 # Try re-inferring r.h.s. in empty context, and use that if it
 
@@ -2984,7 +2984,7 @@ class C(Base):
             sep = "a" if int() else "b"
             reveal_type(sep)  # N: Revealed type is "Union[Literal['a'], Literal['b']]"
         return super().feed_data(sep)
-[builtins fixtures/tuple.pyi]
+[builtins fixtures/primitives.pyi]
 
 [case testLiteralInsideAType]
 from typing_extensions import Literal
 
@@ -19,6 +19,7 @@ class int:
     def __init__(self, x: object = ..., base: int = ...) -> None: pass
     def __add__(self, i: int) -> int: pass
     def __rmul__(self, x: int) -> int: pass
+    def __bool__(self) -> bool: pass
 class float:
     def __float__(self) -> float: pass
     def __add__(self, x: float) -> float: pass