Parenthesize multi-context managers

crates/ruff_python_formatter/src/preview.rs

@@ -33,3 +33,12 @@ pub(crate) const fn is_no_blank_line_before_class_docstring_enabled(
 ) -> bool {
     context.is_preview()
 }
+
+/// Returns `true` if the [`wrap_multiple_context_managers_in_parens`](https://github.com/astral-sh/ruff/issues/8889) preview style is enabled.
+///
+/// Unlike Black, we re-use the same preview style feature flag for [`improved_async_statements_handling`](https://github.com/astral-sh/ruff/issues/8890)
+pub(crate) const fn is_wrap_multiple_context_managers_in_parens_enabled(
+    context: &PyFormatContext,
+) -> bool {
+    context.is_preview()
+}

crates/ruff_python_formatter/src/statement/stmt_with.rs

@@ -9,8 +9,9 @@ use crate::comments::SourceComment;
 use crate::expression::parentheses::parenthesized;
 use crate::other::commas;
 use crate::prelude::*;
+use crate::preview::is_wrap_multiple_context_managers_in_parens_enabled;
 use crate::statement::clause::{clause_body, clause_header, ClauseHeader};
-use crate::PyFormatOptions;
+use crate::{PyFormatOptions, PythonVersion};
 
 #[derive(Default)]
 pub struct FormatStmtWith;
@@ -115,14 +116,22 @@ impl FormatNodeRule<StmtWith> for FormatStmtWith {
 
 /// Returns `true` if the `with` items should be parenthesized, if at least one item expands.
 ///
-/// Black parenthesizes `with` items if there's more than one item and they're already
-/// parenthesized, _or_ there's a single item with a trailing comma.
+/// Parenthesize `with` items if
+/// * The last item has a trailing comma
+/// * There's more than one item and they're already parenthesized
+/// * There's more than one item and the target python version is >= 3.9
 fn should_parenthesize(
     with: &StmtWith,
     options: &PyFormatOptions,
     context: &PyFormatContext,
 ) -> FormatResult<bool> {
-    if has_magic_trailing_comma(with, options, context) {
+    if with.items.len() <= 1 {
+        return Ok(has_magic_trailing_comma(with, options, context));
+    }
+
+    if is_wrap_multiple_context_managers_in_parens_enabled(context)
+        && options.target_version() >= PythonVersion::Py39
+    {
         return Ok(true);
     }