Try

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

@@ -254,3 +254,35 @@ with (
 
 with (foo() as bar, baz() as bop):
     pass
+
+# Trailing comments on items, broken by commas and parentheses.
+with (
+    a
+    as
+    # comment
+    b  # leading comment
+): ...
+
+
+with (
+    a
+    as
+    b,  # leading comment
+    c as d
+): ...
+
+
+with (
+    a
+    as
+    b  # leading comment
+    ,c as d
+): ...
+
+
+with (
+    a as (
+    b  # leading comment
+    )
+    ,c as d
+): ...

crates/ruff_python_formatter/src/comments/placement.rs

@@ -235,7 +235,7 @@ fn handle_enclosed_comment<'a>(
             handle_leading_class_with_decorators_comment(comment, class_def)
         }
         AnyNodeRef::StmtImportFrom(import_from) => handle_import_from_comment(comment, import_from),
-        AnyNodeRef::StmtWith(with_) => handle_with_comment(comment, with_),
+        AnyNodeRef::StmtWith(_) => handle_with_comment(comment, locator),
         AnyNodeRef::ExprCall(_) => handle_call_comment(comment),
         AnyNodeRef::ExprConstant(_) => {
             if let Some(AnyNodeRef::ExprFString(fstring)) = comment.enclosing_parent() {
@@ -1565,7 +1565,7 @@ fn handle_import_from_comment<'a>(
 ///
 /// For example, given:
 /// ```python
-/// with ( # foo
+/// with (  # comment
 ///     CtxManager1() as example1,
 ///     CtxManager2() as example2,
 ///     CtxManager3() as example3,
@@ -1577,17 +1577,59 @@ fn handle_import_from_comment<'a>(
 /// that it remains on the same line as the [`ast::StmtWith`] itself.
 fn handle_with_comment<'a>(
     comment: DecoratedComment<'a>,
-    with_statement: &'a ast::StmtWith,
+    locator: &Locator,
 ) -> CommentPlacement<'a> {
-    if comment.line_position().is_end_of_line()
-        && with_statement.items.first().is_some_and(|with_item| {
-            with_statement.start() < comment.start() && comment.start() < with_item.start()
-        })
-    {
-        CommentPlacement::dangling(comment.enclosing_node(), comment)
-    } else {
-        CommentPlacement::Default(comment)
+    if comment.line_position().is_own_line() {
+        return CommentPlacement::Default(comment);
     }
+
+    if let Some(preceding) = comment.preceding_node() {
+        // If a comment trails a `WithItem` with an `as`, consider attaching it to the optional
+        // variable, rather than to the `WithItem` itself.
+        //
+        // For example, given:
+        // ```python
+        // with (
+        //     a
+        //     as
+        //     b  # comment
+        //     , c as d
+        // ): ...
+        // ```
+        //
+        // The `# comment` should be attached to the optional variable `b`, rather than to the
+        // `WithItem` itself.
+        if let AnyNodeRef::WithItem(ast::WithItem {
+            context_expr: _,
+            optional_vars: Some(optional_vars),
+            range: _,
+        }) = preceding
+        {
+            let tokenizer = SimpleTokenizer::new(
+                locator.contents(),
+                TextRange::new(optional_vars.end(), comment.start()),
+            );
+            if !tokenizer
+                .skip_trivia()
+                .any(|token| token.kind() == SimpleTokenKind::Comma)
+            {
+                return CommentPlacement::trailing(optional_vars.as_ref(), comment);
+            }
+        }
+    } else if let Some(following) = comment.following_node() {
+        // If a comment precedes the first `WithItem`, attach it as dangling:
+        // ```python
+        // with (  # comment
+        //     a as b,
+        //     c as d,
+        // ): ...
+        // ```
+        if comment.start() < following.start() {
+            return CommentPlacement::dangling(comment.enclosing_node(), comment);
+        }
+    }
+
+    CommentPlacement::Default(comment)
 }
 
 /// Handle comments inside comprehensions, e.g.

crates/ruff_python_formatter/src/other/with_item.rs

@@ -33,7 +33,8 @@ impl FormatNodeRule<WithItem> for FormatWithItem {
             write!(f, [space(), text("as"), space()])?;
 
             if trailing_as_comments.is_empty() {
-                write!(f, [optional_vars.format()])?;
+                maybe_parenthesize_expression(optional_vars, item, Parenthesize::IfRequired)
+                    .fmt(f)?;
             } else {
                 write!(
                     f,

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

@@ -260,6 +260,38 @@ with (
 
 with (foo() as bar, baz() as bop):
     pass
+
+# Trailing comments on items, broken by commas and parentheses.
+with (
+    a
+    as
+    # comment
+    b  # leading comment
+): ...
+
+
+with (
+    a
+    as
+    b,  # leading comment
+    c as d
+): ...
+
+
+with (
+    a
+    as
+    b  # leading comment
+    ,c as d
+): ...
+
+
+with (
+    a as (
+    b  # leading comment
+    )
+    ,c as d
+): ...
 ```
 
 ## Output
@@ -290,8 +322,8 @@ with (
 with (
     a as (  # a  # as
         # own line
-        b
-    ),  # b  # comma
+        b  # b
+    ),  # comma
     c,  # c
 ):  # colon
     ...  # body
@@ -299,8 +331,8 @@ with (
 
 with a as (  # a  # as
     # own line
-    bbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbb
-):  # b
+    bbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbb  # b
+):
     pass
 
 
@@ -375,8 +407,8 @@ with (
     a
     # trailing own line comment
 ) as (  # trailing as same line comment
-    b
-):  # trailing b same line comment
+    b  # trailing b same line comment
+):
     ...
 
 with (
@@ -533,6 +565,34 @@ with (
 
 with foo() as bar, baz() as bop:
     pass
+
+# Trailing comments on items, broken by commas and parentheses.
+with a as (
+    # comment
+    b  # leading comment
+):
+    ...
+
+
+with (
+    a as b,  # leading comment
+    c as d,
+):
+    ...
+
+
+with (
+    a as b,  # leading comment
+    c as d,
+):
+    ...
+
+
+with (
+    a as b,  # leading comment
+    c as d,
+):
+    ...
 ```