diff --git a/crates/ruff_python_formatter/resources/test/fixtures/ruff/expression/unary.py b/crates/ruff_python_formatter/resources/test/fixtures/ruff/expression/unary.py
index 89ca82644a..e191045bac 100644
--- a/crates/ruff_python_formatter/resources/test/fixtures/ruff/expression/unary.py
+++ b/crates/ruff_python_formatter/resources/test/fixtures/ruff/expression/unary.py
@@ -151,3 +151,13 @@ if (
   not  # comment
   a):
     ...
+
+# Regression test for: https://github.com/astral-sh/ruff/issues/7423
+if True:
+    if True:
+        if True:
+            if not yn_question(
+                Fore.RED
+                + "WARNING: Removing listed files. Do you really want to continue. yes/n)? "
+            ):
+                pass
diff --git a/crates/ruff_python_formatter/src/expression/expr_unary_op.rs b/crates/ruff_python_formatter/src/expression/expr_unary_op.rs
index 1b58d03571..5057a68693 100644
--- a/crates/ruff_python_formatter/src/expression/expr_unary_op.rs
+++ b/crates/ruff_python_formatter/src/expression/expr_unary_op.rs
@@ -82,8 +82,10 @@ impl NeedsParentheses for ExprUnaryOp {
             context.source(),
         ) {
             OptionalParentheses::Never
+        } else if context.comments().has(self.operand.as_ref()) {
+            OptionalParentheses::Always
         } else {
-            OptionalParentheses::Multiline
+            self.operand.needs_parentheses(self.into(), context)
         }
     }
 }
diff --git a/crates/ruff_python_formatter/tests/snapshots/format@expression__unary.py.snap b/crates/ruff_python_formatter/tests/snapshots/format@expression__unary.py.snap
index 6e87a9a5e7..93114ae769 100644
--- a/crates/ruff_python_formatter/tests/snapshots/format@expression__unary.py.snap
+++ b/crates/ruff_python_formatter/tests/snapshots/format@expression__unary.py.snap
@@ -157,6 +157,16 @@ if (
   not  # comment
   a):
     ...
+
+# Regression test for: https://github.com/astral-sh/ruff/issues/7423
+if True:
+    if True:
+        if True:
+            if not yn_question(
+                Fore.RED
+                + "WARNING: Removing listed files. Do you really want to continue. yes/n)? "
+            ):
+                pass
 ```
 
 ## Output
@@ -323,10 +333,18 @@ if (
 ):
     ...
 
-if (
-    not a  # comment
-):
+if not a:  # comment
     ...
+
+# Regression test for: https://github.com/astral-sh/ruff/issues/7423
+if True:
+    if True:
+        if True:
+            if not yn_question(
+                Fore.RED
+                + "WARNING: Removing listed files. Do you really want to continue. yes/n)? "
+            ):
+                pass
 ```