diff --git a/crates/ruff_linter/resources/test/fixtures/flake8_simplify/SIM103.py b/crates/ruff_linter/resources/test/fixtures/flake8_simplify/SIM103.py
index e1b868888df86..f42b9dc262a80 100644
--- a/crates/ruff_linter/resources/test/fixtures/flake8_simplify/SIM103.py
+++ b/crates/ruff_linter/resources/test/fixtures/flake8_simplify/SIM103.py
@@ -111,3 +111,15 @@ def f():
     if a:
         return False
     return True
+
+
+def f():
+    if not 10 < a:
+        return False
+    return True
+
+
+def f():
+    if 10 < a:
+        return False
+    return True
diff --git a/crates/ruff_linter/src/rules/flake8_simplify/rules/needless_bool.rs b/crates/ruff_linter/src/rules/flake8_simplify/rules/needless_bool.rs
index 34a151a5158c8..1eb1943c89d6d 100644
--- a/crates/ruff_linter/src/rules/flake8_simplify/rules/needless_bool.rs
+++ b/crates/ruff_linter/src/rules/flake8_simplify/rules/needless_bool.rs
@@ -202,11 +202,20 @@ pub(crate) fn needless_bool(checker: &mut Checker, stmt: &Stmt) {
     } else {
         // If the return values are inverted, wrap the condition in a `not`.
         if inverted {
-            Some(Expr::UnaryOp(ast::ExprUnaryOp {
+            if let Expr::UnaryOp(ast::ExprUnaryOp {
                 op: ast::UnaryOp::Not,
-                operand: Box::new(if_test.clone()),
-                range: TextRange::default(),
-            }))
+                operand,
+                ..
+            }) = if_test
+            {
+                Some((**operand).clone())
+            } else {
+                Some(Expr::UnaryOp(ast::ExprUnaryOp {
+                    op: ast::UnaryOp::Not,
+                    operand: Box::new(if_test.clone()),
+                    range: TextRange::default(),
+                }))
+            }
         } else if if_test.is_compare_expr() {
             // If the condition is a comparison, we can replace it with the condition, since we
             // know it's a boolean.
diff --git a/crates/ruff_linter/src/rules/flake8_simplify/snapshots/ruff_linter__rules__flake8_simplify__tests__preview__SIM103_SIM103.py.snap b/crates/ruff_linter/src/rules/flake8_simplify/snapshots/ruff_linter__rules__flake8_simplify__tests__preview__SIM103_SIM103.py.snap
index a71b6622c25cf..1b44533abc17b 100644
--- a/crates/ruff_linter/src/rules/flake8_simplify/snapshots/ruff_linter__rules__flake8_simplify__tests__preview__SIM103_SIM103.py.snap
+++ b/crates/ruff_linter/src/rules/flake8_simplify/snapshots/ruff_linter__rules__flake8_simplify__tests__preview__SIM103_SIM103.py.snap
@@ -213,3 +213,49 @@ SIM103.py:111:5: SIM103 [*] Return the condition `not a` directly
 112     |-        return False
 113     |-    return True
     111 |+    return not a
+114 112 | 
+115 113 | 
+116 114 | def f():
+
+SIM103.py:117:5: SIM103 [*] Return the condition `10 < a` directly
+    |
+116 |   def f():
+117 |       if not 10 < a:
+    |  _____^
+118 | |         return False
+119 | |     return True
+    | |_______________^ SIM103
+    |
+    = help: Replace with `return 10 < a`
+
+ℹ Unsafe fix
+114 114 | 
+115 115 | 
+116 116 | def f():
+117     |-    if not 10 < a:
+118     |-        return False
+119     |-    return True
+    117 |+    return 10 < a
+120 118 | 
+121 119 | 
+122 120 | def f():
+
+SIM103.py:123:5: SIM103 [*] Return the condition `not 10 < a` directly
+    |
+122 |   def f():
+123 |       if 10 < a:
+    |  _____^
+124 | |         return False
+125 | |     return True
+    | |_______________^ SIM103
+    |
+    = help: Replace with `return not 10 < a`
+
+ℹ Unsafe fix
+120 120 | 
+121 121 | 
+122 122 | def f():
+123     |-    if 10 < a:
+124     |-        return False
+125     |-    return True
+    123 |+    return not 10 < a