try a different approach

crates/ruff_python_formatter/src/comments/placement.rs

@@ -1861,16 +1861,10 @@ fn handle_unary_op_comment<'a>(
             | SimpleTokenKind::Plus
             | SimpleTokenKind::Minus
     )));
-    let lparen_start = tokenizer
+    let up_to = tokenizer
         .find(|token| token.kind == SimpleTokenKind::LParen)
-        .map(|lparen| lparen.start());
-    let up_to = lparen_start.unwrap_or(unary_op.operand.start());
-    if lparen_start.is_none()
-        && comment.end() < unary_op.operand.start()
-        && comment.line_position().is_end_of_line()
-    {
-        CommentPlacement::dangling(unary_op, comment)
-    } else if comment.end() < up_to {
+        .map_or(unary_op.operand.start(), |lparen| lparen.start());
+    if comment.end() < up_to {
         CommentPlacement::leading(unary_op, comment)
     } else {
         CommentPlacement::Default(comment)

crates/ruff_python_formatter/src/expression/binary_like.rs

@@ -836,7 +836,8 @@ impl<'a> Operand<'a> {
                 let leading = comments.leading(*expression);
                 if is_expression_parenthesized((*expression).into(), comments.ranges(), source) {
                     leading.iter().any(|comment| {
-                        !comment.is_formatted()
+                        comment.end() <= expression.start()
+                            && !comment.is_formatted()
                             && matches!(
                                 SimpleTokenizer::new(
                                     source,
@@ -922,7 +923,8 @@ impl Format<PyFormatContext<'_>> for Operand<'_> {
             let leading_before_parentheses_end = leading
                 .iter()
                 .rposition(|comment| {
-                    comment.is_unformatted()
+                    comment.end() <= expression.start()
+                        && comment.is_unformatted()
                         && matches!(
                             SimpleTokenizer::new(
                                 f.context().source(),

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

@@ -200,10 +200,21 @@ def foo():
     ):
         pass
 
-# Regression test for https://github.com/astral-sh/ruff/issues/19226
+# Regression tests for https://github.com/astral-sh/ruff/issues/19226
 if '' and (not #
 0):
     pass
+
+if '' and (not #
+(0)
+):
+    pass
+
+if '' and (not
+	(  #
+	0
+)):
+    pass
 ```
 
 ## Output
@@ -322,28 +333,31 @@ if (
 
 ## Trailing operator comments
 
-if (
-    not aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa  # comment
+if (  # comment
+    not aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa
     + bbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbb
 ):
     pass
 
 
 if (
-    ~aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa  # comment
+    # comment
+    ~aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa
     + bbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbb
 ):
     pass
 
 if (
-    -aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa  # comment
+    # comment
+    -aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa
     + bbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbb
 ):
     pass
 
 
 if (
-    +aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa  # comment
+    # comment
+    +aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa
     + bbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbb
 ):
     pass
@@ -368,7 +382,9 @@ if (
 ):
     pass
 
-if not a:  # comment
+if (  # comment
+    not a
+):
     pass
 
 # Regression test for: https://github.com/astral-sh/ruff/issues/7423
@@ -416,9 +432,21 @@ def foo():
         pass
 
 
-# Regression test for https://github.com/astral-sh/ruff/issues/19226
+# Regression tests for https://github.com/astral-sh/ruff/issues/19226
+if "" and (  #
+    not 0
+):
+    pass
+
+if "" and (  #
+    not (0)
+):
+    pass
+
 if "" and (
-    not 0  #
+    not (  #
+        0
+    )
 ):
     pass
 ```