diff --git a/crates/ruff_python_formatter/resources/test/fixtures/ruff/expression/boolean_operation.py b/crates/ruff_python_formatter/resources/test/fixtures/ruff/expression/boolean_operation.py
index 00bfa3e943117..f9254eceb53ee 100644
--- a/crates/ruff_python_formatter/resources/test/fixtures/ruff/expression/boolean_operation.py
+++ b/crates/ruff_python_formatter/resources/test/fixtures/ruff/expression/boolean_operation.py
@@ -73,3 +73,13 @@
     isinstance(aaaaaaaaaaaaaaaaaaaaaaa, bbbbbbbbb) and numpy or isinstance(ccccccccccc, dddddd)
 ):
     pass
+
+if not (
+    isinstance(aaaaaaaaaaaaaaaaaaaaaaa, bbbbbbbbb) or xxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxx + yyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyy and isinstance(ccccccccccc, dddddd)
+):
+    pass
+
+if not (
+    isinstance(aaaaaaaaaaaaaaaaaaaaaaa, bbbbbbbbb) and xxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxx + yyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyy or isinstance(ccccccccccc, dddddd)
+):
+    pass
diff --git a/crates/ruff_python_formatter/tests/snapshots/format@expression__boolean_operation.py.snap b/crates/ruff_python_formatter/tests/snapshots/format@expression__boolean_operation.py.snap
index b769a8759e10e..e80c39bd9ad8f 100644
--- a/crates/ruff_python_formatter/tests/snapshots/format@expression__boolean_operation.py.snap
+++ b/crates/ruff_python_formatter/tests/snapshots/format@expression__boolean_operation.py.snap
@@ -79,6 +79,16 @@ if not (
     isinstance(aaaaaaaaaaaaaaaaaaaaaaa, bbbbbbbbb) and numpy or isinstance(ccccccccccc, dddddd)
 ):
     pass
+
+if not (
+    isinstance(aaaaaaaaaaaaaaaaaaaaaaa, bbbbbbbbb) or xxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxx + yyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyy and isinstance(ccccccccccc, dddddd)
+):
+    pass
+
+if not (
+    isinstance(aaaaaaaaaaaaaaaaaaaaaaa, bbbbbbbbb) and xxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxx + yyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyy or isinstance(ccccccccccc, dddddd)
+):
+    pass
 ```
 
 ## Output
@@ -162,6 +172,22 @@ if not (
     or isinstance(ccccccccccc, dddddd)
 ):
     pass
+
+if not (
+    isinstance(aaaaaaaaaaaaaaaaaaaaaaa, bbbbbbbbb)
+    or xxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxx
+    + yyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyy
+    and isinstance(ccccccccccc, dddddd)
+):
+    pass
+
+if not (
+    isinstance(aaaaaaaaaaaaaaaaaaaaaaa, bbbbbbbbb)
+    and xxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxx
+    + yyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyy
+    or isinstance(ccccccccccc, dddddd)
+):
+    pass
 ```