diff --git a/packages/pyright-internal/src/tests/checker.test.ts b/packages/pyright-internal/src/tests/checker.test.ts
index da8476e5b..b157eecf7 100644
--- a/packages/pyright-internal/src/tests/checker.test.ts
+++ b/packages/pyright-internal/src/tests/checker.test.ts
@@ -163,6 +163,11 @@ test('With2', () => {
     TestUtils.validateResults(analysisResults, 3);
 });
 
+test('context manager where __exit__ returns bool | None', () => {
+    const analysisResults = TestUtils.typeAnalyzeSampleFiles(['withBased.py']);
+    TestUtils.validateResultsButBased(analysisResults, { unreachableCodes: [{ line: 47 }], unusedCodes: undefined });
+});
+
 test('With3', () => {
     const analysisResults = TestUtils.typeAnalyzeSampleFiles(['with3.py']);
 
diff --git a/packages/pyright-internal/src/tests/samples/withBased.py b/packages/pyright-internal/src/tests/samples/withBased.py
new file mode 100644
index 000000000..1ff09abbf
--- /dev/null
+++ b/packages/pyright-internal/src/tests/samples/withBased.py
@@ -0,0 +1,48 @@
+import contextlib
+from types import TracebackType
+from typing import Iterator, Literal
+
+from typing_extensions import assert_never
+
+class BoolOrNone(contextlib.AbstractContextManager[None]):
+    def __exit__(
+        self,
+        __exc_type: type[BaseException] | None,
+        __exc_value: BaseException | None,
+        __traceback: TracebackType | None,
+    ) -> bool | None:
+        ...
+
+def _():
+    with BoolOrNone():
+        raise Exception
+    print(1)  # reachable
+
+class TrueOrNone(contextlib.AbstractContextManager[None]):
+    def __exit__(
+        self,
+        __exc_type: type[BaseException] | None,
+        __exc_value: BaseException | None,
+        __traceback: TracebackType | None,
+    ) -> Literal[True] | None:
+        ...
+
+def _():
+    with TrueOrNone():
+        raise Exception
+    print(1)  # reachable
+
+
+class FalseOrNone(contextlib.AbstractContextManager[None]):
+    def __exit__(
+        self,
+        __exc_type: type[BaseException] | None,
+        __exc_value: BaseException | None,
+        __traceback: TracebackType | None,
+    ) -> Literal[False] | None:
+        ...
+
+def _():
+    with FalseOrNone():
+        raise Exception
+    print(1)  # unreachable
\ No newline at end of file
diff --git a/packages/pyright-internal/src/tests/testUtils.ts b/packages/pyright-internal/src/tests/testUtils.ts
index 2becc39a6..7f71e0003 100644
--- a/packages/pyright-internal/src/tests/testUtils.ts
+++ b/packages/pyright-internal/src/tests/testUtils.ts
@@ -245,7 +245,11 @@ export const validateResultsButBased = (allResults: FileAnalysisResult[], expect
                 code: result.getRule() as DiagnosticRule | undefined,
             })
         );
-        const expectedResult = expectedResults[diagnosticType] ?? [];
-        expect(new Set(actualResult)).toEqual(new Set(expectedResult.map(expect.objectContaining)));
+        const expectedResult = expectedResults[diagnosticType];
+        // if it's explicitly in the expected results as undefined, that means we don't care.
+        // if it's not in the expected results at all, then check it
+        if (!(diagnosticType in expectedResults) || expectedResult !== undefined) {
+            expect(new Set(actualResult)).toEqual(new Set((expectedResult ?? []).map(expect.objectContaining)));
+        }
     }
 };