Fix invalid syntax for binary expression in unary op (#5370)

Cargo.lock

@@ -2088,6 +2088,7 @@ dependencies = [
  "serde",
  "serde_json",
  "similar",
+ "smallvec",
 ]
 
 [[package]]

crates/ruff_python_formatter/Cargo.toml

@@ -26,6 +26,7 @@ once_cell = { workspace = true }
 rustc-hash = { workspace = true }
 rustpython-parser = { workspace = true }
 serde = { workspace = true, optional = true }
+smallvec = { workspace = true }
 
 [dev-dependencies]
 ruff_formatter = { path = "../ruff_formatter", features = ["serde"]}

crates/ruff_python_formatter/resources/test/fixtures/ruff/expression/binary.py

@@ -10,6 +10,19 @@
     b
 )
 
+(
+    # leading left most comment
+    aaaaaaaa
+    +  # trailing operator comment
+    # leading b comment
+    b # trailing b comment
+    # trailing b ownline comment
+    +  # trailing second operator comment
+    # leading c comment
+    c # trailing c comment
+    # trailing own line comment
+ )
+
 
 # Black breaks the right side first for the following expressions:
 aaaaaaaaaaaaaa + caaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaal(argument1, argument2, argument3)

crates/ruff_python_formatter/resources/test/fixtures/ruff/expression/unary.py

@@ -136,3 +136,7 @@ if (
 if not \
     a:
     pass
+
+# Regression: https://github.com/astral-sh/ruff/issues/5338
+if a and not aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa & aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa:
+    ...

crates/ruff_python_formatter/resources/test/fixtures/ruff/statement/class_definition.py

@@ -32,5 +32,8 @@ class Test((Aaaa)):
 class Test(aaaaaaaaaaaaaaa + bbbbbbbbbbbbbbbbbbbbbb + cccccccccccccccccccccccc + dddddddddddddddddddddd + eeeeeeeee, ffffffffffffffffff, gggggggggggggggggg):
     pass
 
+class Test(aaaaaaaaaaaaaaa + bbbbbbbbbbbbbbbbbbbbbb * cccccccccccccccccccccccc + dddddddddddddddddddddd + eeeeeeeee, ffffffffffffffffff, gggggggggggggggggg):
+    pass
+
 class Test(Aaaa): # trailing comment
     pass

crates/ruff_python_formatter/src/expression/binary_like.rs

@@ -5,7 +5,7 @@ use rustpython_parser::ast::{self, Expr};
 
 use ruff_formatter::{format_args, write};
 
-use crate::expression::parentheses::Parentheses;
+use crate::expression::parentheses::{is_expression_parenthesized, Parentheses};
 use crate::prelude::*;
 
 /// Trait to implement a binary like syntax that has a left operand, an operator, and a right operand.
@@ -24,7 +24,7 @@ pub(super) trait FormatBinaryLike<'ast> {
         let right = self.right()?;
 
         let layout = if parentheses == Some(Parentheses::Custom) {
-            self.binary_layout()
+            self.binary_layout(f.context().contents())
         } else {
             BinaryLayout::Default
         };
@@ -113,9 +113,9 @@ pub(super) trait FormatBinaryLike<'ast> {
     }
 
     /// Determines which binary layout to use.
-    fn binary_layout(&self) -> BinaryLayout {
+    fn binary_layout(&self, source: &str) -> BinaryLayout {
         if let (Ok(left), Ok(right)) = (self.left(), self.right()) {
-            BinaryLayout::from_left_right(left, right)
+            BinaryLayout::from_left_right(left, right, source)
         } else {
             BinaryLayout::Default
         }
@@ -134,8 +134,8 @@ pub(super) trait FormatBinaryLike<'ast> {
     fn operator(&self) -> Self::FormatOperator;
 }
 
-fn can_break_expr(expr: &Expr) -> bool {
+fn can_break_expr(expr: &Expr, source: &str) -> bool {
-    match expr {
+    let can_break = match expr {
         Expr::Tuple(ast::ExprTuple {
             elts: expressions, ..
         })
@@ -153,12 +153,11 @@ fn can_break_expr(expr: &Expr) -> bool {
             !(args.is_empty() && keywords.is_empty())
         }
         Expr::ListComp(_) | Expr::SetComp(_) | Expr::DictComp(_) | Expr::GeneratorExp(_) => true,
-        Expr::UnaryOp(ast::ExprUnaryOp { operand, .. }) => match operand.as_ref() {
+        Expr::UnaryOp(ast::ExprUnaryOp { operand, .. }) => can_break_expr(operand.as_ref(), source),
-            Expr::BinOp(_) => true,
-            _ => can_break_expr(operand.as_ref()),
-        },
         _ => false,
-    }
+    };
+
+    can_break || is_expression_parenthesized(expr.into(), source)
 }
 
 #[derive(Copy, Clone, Debug, Eq, PartialEq)]
@@ -206,8 +205,8 @@ pub(super) enum BinaryLayout {
 }
 
 impl BinaryLayout {
-    pub(super) fn from_left_right(left: &Expr, right: &Expr) -> BinaryLayout {
+    pub(super) fn from_left_right(left: &Expr, right: &Expr, source: &str) -> BinaryLayout {
-        match (can_break_expr(left), can_break_expr(right)) {
+        match (can_break_expr(left, source), can_break_expr(right, source)) {
             (false, false) => BinaryLayout::Default,
             (true, false) => BinaryLayout::ExpandLeft,
             (false, true) => BinaryLayout::ExpandRight,

crates/ruff_python_formatter/src/expression/expr_bin_op.rs

@@ -1,4 +1,4 @@
-use crate::comments::{trailing_comments, Comments};
+use crate::comments::{trailing_comments, trailing_node_comments, Comments};
 use crate::expression::binary_like::{BinaryLayout, FormatBinaryLike};
 use crate::expression::parentheses::{
     default_expression_needs_parentheses, NeedsParentheses, Parenthesize,
@@ -10,6 +10,8 @@ use ruff_formatter::{write, FormatOwnedWithRule, FormatRefWithRule, FormatRuleWi
 use rustpython_parser::ast::{
     Constant, Expr, ExprAttribute, ExprBinOp, ExprConstant, ExprUnaryOp, Operator, UnaryOp,
 };
+use smallvec::SmallVec;
+use std::iter;
 
 #[derive(Default)]
 pub struct FormatExprBinOp {
@@ -40,41 +42,68 @@ impl<'ast> FormatBinaryLike<'ast> for ExprBinOp {
     type FormatOperator = FormatOwnedWithRule<Operator, FormatOperator, PyFormatContext<'ast>>;
 
     fn fmt_default(&self, f: &mut PyFormatter<'ast, '_>) -> FormatResult<()> {
-        let ExprBinOp {
-            range: _,
-            left,
-            op,
-            right,
-        } = self;
-
         let comments = f.context().comments().clone();
-        let operator_comments = comments.dangling_comments(self);
-        let needs_space = !is_simple_power_expression(self);
 
-        let before_operator_space = if needs_space {
+        let format_inner = format_with(|f| {
-            soft_line_break_or_space()
+            let binary_chain: SmallVec<[&ExprBinOp; 4]> =
-        } else {
+                iter::successors(Some(self), |parent| parent.left.as_bin_op_expr()).collect();
-            soft_line_break()
-        };
 
-        write!(
+            // SAFETY: `binary_chain` is guaranteed not to be empty because it always contains the current expression.
-            f,
+            let left_most = binary_chain.last().unwrap();
-            [
-                left.format(),
-                before_operator_space,
-                op.format(),
-                trailing_comments(operator_comments),
-            ]
-        )?;
 
-        // Format the operator on its own line if the right side has any leading comments.
+            // Format the left most expression
-        if comments.has_leading_comments(right.as_ref()) {
+            group(&left_most.left.format()).fmt(f)?;
-            write!(f, [hard_line_break()])?;
-        } else if needs_space {
-            write!(f, [space()])?;
-        }
 
-        write!(f, [group(&right.format())])
+            // Iterate upwards in the binary expression tree and, for each level, format the operator
+            // and the right expression.
+            for current in binary_chain.into_iter().rev() {
+                let ExprBinOp {
+                    range: _,
+                    left: _,
+                    op,
+                    right,
+                } = current;
+
+                let operator_comments = comments.dangling_comments(current);
+                let needs_space = !is_simple_power_expression(current);
+
+                let before_operator_space = if needs_space {
+                    soft_line_break_or_space()
+                } else {
+                    soft_line_break()
+                };
+
+                write!(
+                    f,
+                    [
+                        before_operator_space,
+                        op.format(),
+                        trailing_comments(operator_comments),
+                    ]
+                )?;
+
+                // Format the operator on its own line if the right side has any leading comments.
+                if comments.has_leading_comments(right.as_ref()) || !operator_comments.is_empty() {
+                    hard_line_break().fmt(f)?;
+                } else if needs_space {
+                    space().fmt(f)?;
+                }
+
+                group(&right.format()).fmt(f)?;
+
+                // It's necessary to format the trailing comments because the code bypasses
+                // `FormatNodeRule::fmt` for the nested binary expressions.
+                // Don't call the formatting function for the most outer binary expression because
+                // these comments have already been formatted.
+                if current != self {
+                    trailing_node_comments(current).fmt(f)?;
+                }
+            }
+
+            Ok(())
+        });
+
+        group(&format_inner).fmt(f)
     }
 
     fn left(&self) -> FormatResult<&Expr> {
@@ -162,7 +191,7 @@ impl NeedsParentheses for ExprBinOp {
     ) -> Parentheses {
         match default_expression_needs_parentheses(self.into(), parenthesize, source, comments) {
             Parentheses::Optional => {
-                if self.binary_layout() == BinaryLayout::Default
+                if self.binary_layout(source) == BinaryLayout::Default
                     || comments.has_leading_comments(self.right.as_ref())
                     || comments.has_dangling_comments(self)
                 {

crates/ruff_python_formatter/src/expression/expr_bool_op.rs

@@ -31,9 +31,9 @@ impl FormatNodeRule<ExprBoolOp> for FormatExprBoolOp {
 impl<'ast> FormatBinaryLike<'ast> for ExprBoolOp {
     type FormatOperator = FormatOwnedWithRule<BoolOp, FormatBoolOp, PyFormatContext<'ast>>;
 
-    fn binary_layout(&self) -> BinaryLayout {
+    fn binary_layout(&self, source: &str) -> BinaryLayout {
         match self.values.as_slice() {
-            [left, right] => BinaryLayout::from_left_right(left, right),
+            [left, right] => BinaryLayout::from_left_right(left, right, source),
             [..] => BinaryLayout::Default,
         }
     }
@@ -93,7 +93,7 @@ impl NeedsParentheses for ExprBoolOp {
         comments: &Comments,
     ) -> Parentheses {
         match default_expression_needs_parentheses(self.into(), parenthesize, source, comments) {
-            Parentheses::Optional => match self.binary_layout() {
+            Parentheses::Optional => match self.binary_layout(source) {
                 BinaryLayout::Default => Parentheses::Optional,
 
                 BinaryLayout::ExpandRight

crates/ruff_python_formatter/src/expression/expr_compare.rs

@@ -34,10 +34,10 @@ impl FormatNodeRule<ExprCompare> for FormatExprCompare {
 impl<'ast> FormatBinaryLike<'ast> for ExprCompare {
     type FormatOperator = FormatOwnedWithRule<CmpOp, FormatCmpOp, PyFormatContext<'ast>>;
 
-    fn binary_layout(&self) -> BinaryLayout {
+    fn binary_layout(&self, source: &str) -> BinaryLayout {
         if self.ops.len() == 1 {
             match self.comparators.as_slice() {
-                [right] => BinaryLayout::from_left_right(&self.left, right),
+                [right] => BinaryLayout::from_left_right(&self.left, right, source),
                 [..] => BinaryLayout::Default,
             }
         } else {
@@ -102,7 +102,7 @@ impl NeedsParentheses for ExprCompare {
         comments: &Comments,
     ) -> Parentheses {
         match default_expression_needs_parentheses(self.into(), parenthesize, source, comments) {
-            parentheses @ Parentheses::Optional => match self.binary_layout() {
+            parentheses @ Parentheses::Optional => match self.binary_layout(source) {
                 BinaryLayout::Default => parentheses,
 
                 BinaryLayout::ExpandRight

crates/ruff_python_formatter/src/expression/mod.rs

@@ -10,7 +10,7 @@ use ruff_formatter::{
 };
 use rustpython_parser::ast::Expr;
 
-mod binary_like;
+pub(crate) mod binary_like;
 pub(crate) mod expr_attribute;
 pub(crate) mod expr_await;
 pub(crate) mod expr_bin_op;

crates/ruff_python_formatter/tests/snapshots/black_compatibility@comments6.py.snap

@@ -147,7 +147,7 @@ aaaaaaaaaaaaa, bbbbbbbbb = map(list, map(itertools.chain.from_iterable, zip(*ite
      an_element_with_a_long_value = calls() or more_calls() and more()  # type: bool
  
      tup = (
-@@ -100,19 +98,35 @@
+@@ -100,19 +98,32 @@
      )
  
      c = call(
@@ -169,10 +169,7 @@ aaaaaaaaaaaaa, bbbbbbbbb = map(list, map(itertools.chain.from_iterable, zip(*ite
  
 -AAAAAAAAAAAAA = [AAAAAAAAAAAAA] + SHARED_AAAAAAAAAAAAA + USER_AAAAAAAAAAAAA + AAAAAAAAAAAAA  # type: ignore
 +AAAAAAAAAAAAA = (
-+    [AAAAAAAAAAAAA]
++    [AAAAAAAAAAAAA] + SHARED_AAAAAAAAAAAAA + USER_AAAAAAAAAAAAA + AAAAAAAAAAAAA
-+    + SHARED_AAAAAAAAAAAAA
-+    + USER_AAAAAAAAAAAAA
-+    + AAAAAAAAAAAAA
 +)  # type: ignore
  
  call_to_some_function_asdf(
@@ -308,10 +305,7 @@ def func(
 result = "xxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxx"  # aaa
 
 AAAAAAAAAAAAA = (
-    [AAAAAAAAAAAAA]
+    [AAAAAAAAAAAAA] + SHARED_AAAAAAAAAAAAA + USER_AAAAAAAAAAAAA + AAAAAAAAAAAAA
-    + SHARED_AAAAAAAAAAAAA
-    + USER_AAAAAAAAAAAAA
-    + AAAAAAAAAAAAA
 )  # type: ignore
 
 call_to_some_function_asdf(

crates/ruff_python_formatter/tests/snapshots/black_compatibility@expression.py.snap

@@ -274,11 +274,20 @@ last_call()
  Name
  None
  True
-@@ -30,33 +31,39 @@
+@@ -23,40 +24,46 @@
+ 1 >> v2
+ 1 % finished
+ 1 + v2 - v3 * 4 ^ 5**v6 / 7 // 8
+-((1 + v2) - (v3 * 4)) ^ (((5**v6) / 7) // 8)
++(1 + v2 - (v3 * 4)) ^ (5**v6 / 7 // 8)
+ not great
+ ~great
+ +value
  -1
  ~int and not v1 ^ 123 + v2 | True
- (~int) and (not ((v1 ^ (123 + v2)) | True))
+-(~int) and (not ((v1 ^ (123 + v2)) | True))
 -+(really ** -(confusing ** ~(operator**-precedence)))
++(~int) and (not (v1 ^ (123 + v2) | True))
 ++really ** -confusing ** ~operator**-precedence
  flags & ~select.EPOLLIN and waiters.write_task is not None
 -lambda arg: None
@@ -638,13 +647,13 @@ v1 << 2
 1 >> v2
 1 % finished
 1 + v2 - v3 * 4 ^ 5**v6 / 7 // 8
-((1 + v2) - (v3 * 4)) ^ (((5**v6) / 7) // 8)
+(1 + v2 - (v3 * 4)) ^ (5**v6 / 7 // 8)
 not great
 ~great
 +value
 -1
 ~int and not v1 ^ 123 + v2 | True
-(~int) and (not ((v1 ^ (123 + v2)) | True))
+(~int) and (not (v1 ^ (123 + v2) | True))
 +really ** -confusing ** ~operator**-precedence
 flags & ~select.EPOLLIN and waiters.write_task is not None
 lambda x: True

crates/ruff_python_formatter/tests/snapshots/black_compatibility@fmtonoff.py.snap

@@ -202,11 +202,11 @@ d={'a':1,
  #!/usr/bin/env python3
 -import asyncio
 -import sys
+-
+-from third_party import X, Y, Z
 +NOT_YET_IMPLEMENTED_StmtImport
 +NOT_YET_IMPLEMENTED_StmtImport
  
--from third_party import X, Y, Z
--
 -from library import some_connection, some_decorator
 +NOT_YET_IMPLEMENTED_StmtImportFrom
  
@@ -306,7 +306,7 @@ d={'a':1,
      h: str = "",
      i: str = r"",
  ):
-@@ -64,55 +86,55 @@
+@@ -64,55 +86,54 @@
  
  something = {
      # fmt: off
@@ -327,8 +327,7 @@ d={'a':1,
 +            "some big and",
 +            "complex subscript",
 +            # fmt: on
-+            goes
++            goes + here,
-+            + here,
 +            andhere,
 +        )
      ]
@@ -382,7 +381,7 @@ d={'a':1,
      # fmt: on
  
  
-@@ -133,10 +155,10 @@
+@@ -133,10 +154,10 @@
      """Another known limitation."""
      # fmt: on
      # fmt: off
@@ -397,7 +396,7 @@ d={'a':1,
      # fmt: on
      # fmt: off
      # ...but comments still get reformatted even though they should not be
-@@ -151,12 +173,10 @@
+@@ -151,12 +172,10 @@
                  ast_args.kw_defaults,
                  parameters,
                  implicit_default=True,
@@ -412,17 +411,16 @@ d={'a':1,
          # fmt: on
      _type_comment_re = re.compile(
          r"""
-@@ -179,7 +199,8 @@
+@@ -179,7 +198,7 @@
          $
          """,
          # fmt: off
 -        re.MULTILINE|re.VERBOSE
-+        re.MULTILINE
++        re.MULTILINE | re.VERBOSE,
-+        | re.VERBOSE,
          # fmt: on
      )
  
-@@ -217,8 +238,7 @@
+@@ -217,8 +236,7 @@
      xxxxxxxxxx_xxxxxxxxxxx_xxxxxxx_xxxxxxxxx=5,
  )
  # fmt: off
@@ -538,8 +536,7 @@ def subscriptlist():
             "some big and",
             "complex subscript",
             # fmt: on
-            goes
+            goes + here,
-            + here,
             andhere,
         )
     ]
@@ -640,8 +637,7 @@ def long_lines():
         $
         """,
         # fmt: off
-        re.MULTILINE
+        re.MULTILINE | re.VERBOSE,
-        | re.VERBOSE,
         # fmt: on
     )
 

crates/ruff_python_formatter/tests/snapshots/black_compatibility@function.py.snap

@@ -111,14 +111,14 @@ def __await__(): return (yield)
  #!/usr/bin/env python3
 -import asyncio
 -import sys
--
--from third_party import X, Y, Z
 +NOT_YET_IMPLEMENTED_StmtImport
 +NOT_YET_IMPLEMENTED_StmtImport
  
--from library import some_connection, some_decorator
+-from third_party import X, Y, Z
 +NOT_YET_IMPLEMENTED_StmtImportFrom
  
+-from library import some_connection, some_decorator
+-
 -f"trigger 3.6 mode"
 +NOT_YET_IMPLEMENTED_StmtImportFrom
 +NOT_YET_IMPLEMENTED_ExprJoinedStr
@@ -215,17 +215,7 @@ def __await__(): return (yield)
          )
      _type_comment_re = re.compile(
          r"""
-@@ -118,7 +124,8 @@
+@@ -135,14 +141,8 @@
-         )
-         $
-         """,
--        re.MULTILINE | re.VERBOSE,
-+        re.MULTILINE
-+        | re.VERBOSE,
-     )
- 
- 
-@@ -135,14 +142,8 @@
      a,
      **kwargs,
  ) -> A:
@@ -373,8 +363,7 @@ def long_lines():
         )
         $
         """,
-        re.MULTILINE
+        re.MULTILINE | re.VERBOSE,
-        | re.VERBOSE,
     )
 
 

crates/ruff_python_formatter/tests/snapshots/black_compatibility@slices.py.snap

@@ -115,12 +115,13 @@ x[
  ham[lower + offset : upper + offset]
  
  slice[::, ::]
-@@ -50,10 +50,14 @@
+@@ -49,11 +49,14 @@
+ 
  slice[
      # A
-     1
+-    1
 -    + 2 :
-+    + 2 : 
++    1 + 2 : 
      # B
 -    3 :
 +    3 : 
@@ -189,8 +190,7 @@ slice[
 
 slice[
     # A
-    1
+    1 + 2 : 
-    + 2 : 
     # B
     3 : 
     # C

crates/ruff_python_formatter/tests/snapshots/format@expression__binary.py.snap

@@ -16,6 +16,19 @@ input_file: crates/ruff_python_formatter/resources/test/fixtures/ruff/expression
     b
 )
 
+(
+    # leading left most comment
+    aaaaaaaa
+    +  # trailing operator comment
+    # leading b comment
+    b # trailing b comment
+    # trailing b ownline comment
+    +  # trailing second operator comment
+    # leading c comment
+    c # trailing c comment
+    # trailing own line comment
+ )
+
 
 # Black breaks the right side first for the following expressions:
 aaaaaaaaaaaaaa + caaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaal(argument1, argument2, argument3)
@@ -204,7 +217,8 @@ for user_id in set(target_user_ids) - {u.user_id for u in updates}:
 ```py
 (
     aaaaaaaa
-    + b  # trailing operator comment  # trailing right comment
+    +  # trailing operator comment
+    b  # trailing right comment
 )
 
 
@@ -215,6 +229,19 @@ for user_id in set(target_user_ids) - {u.user_id for u in updates}:
     b
 )
 
+(
+    # leading left most comment
+    aaaaaaaa
+    +  # trailing operator comment
+    # leading b comment
+    b  # trailing b comment
+    # trailing b ownline comment
+    +  # trailing second operator comment
+    # leading c comment
+    c  # trailing c comment
+    # trailing own line comment
+)
+
 
 # Black breaks the right side first for the following expressions:
 aaaaaaaaaaaaaa + caaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaal(
@@ -269,8 +296,7 @@ not (aaaaaaaaaaaaaa + {NOT_IMPLEMENTED_set_value for value in NOT_IMPLEMENTED_se
 # leading comment
 (
     # comment
-    content
+    content + b
-    + b
 )
 
 
@@ -417,8 +443,7 @@ if (
     &
     (
         # comment
-        a
+        a + b
-        + b
     )
 ):
     ...
@@ -433,8 +458,7 @@ if (
     ]
     &
     # comment
-    a
+    a + b
-    + b
 ):
     ...
 

crates/ruff_python_formatter/tests/snapshots/format@expression__unary.py.snap

@@ -142,6 +142,10 @@ if (
 if not \
     a:
     pass
+
+# Regression: https://github.com/astral-sh/ruff/issues/5338
+if a and not aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa & aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa:
+    ...
 ```
 
 ## Output
@@ -253,10 +257,8 @@ if aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa & (
     pass
 
 if (
-    not (
+    not aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa
-        aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa
+    + bbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbb
-        + bbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbb
-    )
     & aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa
 ):
     pass
@@ -295,6 +297,14 @@ if (
 
 if not a:
     pass
+
+# Regression: https://github.com/astral-sh/ruff/issues/5338
+if (
+    a
+    and not aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa
+    & aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa
+):
+    ...
 ```
 
 

crates/ruff_python_formatter/tests/snapshots/format@statement__call.py.snap

@@ -125,8 +125,7 @@ f(
 f(
     this_is_a_very_long_argument_asökdhflakjslaslhfdlaffahflahsöfdhasägporejfäalkdsjäfalisjäfdlkasjd,
     these_arguments_have_values_that_need_to_break_because_they_are_too_long1=(
-        100000
+        100000 - 100000000000
-        - 100000000000
     ),
     these_arguments_have_values_that_need_to_break_because_they_are_too_long2="akshfdlakjsdfad"
     + "asdfasdfa",

crates/ruff_python_formatter/tests/snapshots/format@statement__class_definition.py.snap

@@ -38,6 +38,9 @@ class Test((Aaaa)):
 class Test(aaaaaaaaaaaaaaa + bbbbbbbbbbbbbbbbbbbbbb + cccccccccccccccccccccccc + dddddddddddddddddddddd + eeeeeeeee, ffffffffffffffffff, gggggggggggggggggg):
     pass
 
+class Test(aaaaaaaaaaaaaaa + bbbbbbbbbbbbbbbbbbbbbb * cccccccccccccccccccccccc + dddddddddddddddddddddd + eeeeeeeee, ffffffffffffffffff, gggggggggggggggggg):
+    pass
+
 class Test(Aaaa): # trailing comment
     pass
 ```
@@ -88,6 +91,17 @@ class Test(
     pass
 
 
+class Test(
+    aaaaaaaaaaaaaaa
+    + bbbbbbbbbbbbbbbbbbbbbb * cccccccccccccccccccccccc
+    + dddddddddddddddddddddd
+    + eeeeeeeee,
+    ffffffffffffffffff,
+    gggggggggggggggggg,
+):
+    pass
+
+
 class Test(Aaaa):  # trailing comment
     pass
 ```

crates/ruff_python_formatter/tests/snapshots/format@statement__with.py.snap

@@ -114,8 +114,7 @@ with a:  # should remove brackets
 # WithItem allow the `aa + bb` content expression to be wrapped
 with (
     (
-        aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa
+        aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa + bbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbb
-        + bbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbb
     ) as c,
 ):
     ...