diff --git a/mypy/checker.py b/mypy/checker.py
index 3734f3170790f..bf6c8423c12b1 100644
--- a/mypy/checker.py
+++ b/mypy/checker.py
@@ -4469,7 +4469,7 @@ 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
diff --git a/test-data/unit/check-literal.test b/test-data/unit/check-literal.test
index fb97bec051e14..856bc941435de 100644
--- a/test-data/unit/check-literal.test
+++ b/test-data/unit/check-literal.test
@@ -2980,7 +2980,7 @@ 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
diff --git a/test-data/unit/fixtures/primitives.pyi b/test-data/unit/fixtures/primitives.pyi
index fc220a4e2ee0c..2f8623c79b9ff 100644
--- a/test-data/unit/fixtures/primitives.pyi
+++ b/test-data/unit/fixtures/primitives.pyi
@@ -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