diff --git a/crates/ruff_python_formatter/src/comments/placement.rs b/crates/ruff_python_formatter/src/comments/placement.rs
index d0906d24b6..1f763563f0 100644
--- a/crates/ruff_python_formatter/src/comments/placement.rs
+++ b/crates/ruff_python_formatter/src/comments/placement.rs
@@ -1861,11 +1861,17 @@ fn handle_unary_op_comment<'a>(
             | SimpleTokenKind::Plus
             | SimpleTokenKind::Minus
     )));
-    let up_to = tokenizer
+    let lparen_start = tokenizer
         .find(|token| token.kind == SimpleTokenKind::LParen)
-        .map_or(unary_op.operand.start(), |lparen| lparen.start());
-    if comment.end() < up_to {
-        CommentPlacement::leading(&*unary_op.operand, comment)
+        .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 {
+        CommentPlacement::leading(unary_op, comment)
     } else {
         CommentPlacement::Default(comment)
     }
diff --git a/crates/ruff_python_formatter/tests/snapshots/format@expression__unary.py.snap b/crates/ruff_python_formatter/tests/snapshots/format@expression__unary.py.snap
index 2cdde4e0d9..74ba326706 100644
--- a/crates/ruff_python_formatter/tests/snapshots/format@expression__unary.py.snap
+++ b/crates/ruff_python_formatter/tests/snapshots/format@expression__unary.py.snap
@@ -254,35 +254,31 @@ if +(
     pass
 
 if (
-    not
     # comment
-    aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa
+    not aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa
     + bbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbb
 ):
     pass
 
 
 if (
-    ~
     # comment
-    aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa
+    ~aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa
     + bbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbb
 ):
     pass
 
 if (
-    -
     # comment
-    aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa
+    -aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa
     + bbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbb
 ):
     pass
 
 
 if (
-    +
     # comment
-    aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa
+    +aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa
     + bbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbb
 ):
     pass
@@ -291,8 +287,8 @@ if (
 
 if (
     # unary comment
-    not # operand comment
-    (
+    # operand comment
+    not (
         # comment
         aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa
         + bbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbb
@@ -327,35 +323,27 @@ if (
 ## Trailing operator comments
 
 if (
-    not
-    # comment
-    aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa
+    not aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa  # comment
     + bbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbb
 ):
     pass
 
 
 if (
-    ~
-    # comment
-    aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa
+    ~aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa  # comment
     + bbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbb
 ):
     pass
 
 if (
-    -
-    # comment
-    aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa
+    -aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa  # comment
     + bbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbb
 ):
     pass
 
 
 if (
-    +
-    # comment
-    aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa
+    +aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa  # comment
     + bbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbb
 ):
     pass
@@ -375,17 +363,12 @@ if (
     pass
 
 if (
-    not
     # comment
-    a
+    not a
 ):
     pass
 
-if (
-    not
-    # comment
-    a
-):
+if not a:  # comment
     pass
 
 # Regression test for: https://github.com/astral-sh/ruff/issues/7423
@@ -401,9 +384,9 @@ if True:
 # Regression test for: https://github.com/astral-sh/ruff/issues/7448
 x = (
     # a
-    not # b
+    # b
     # c
-    (  # d
+    not (  # d
         # e
         True
     )
@@ -435,9 +418,7 @@ def foo():
 
 # Regression test for https://github.com/astral-sh/ruff/issues/19226
 if "" and (
-    not
-    #
-    0
+    not 0  #
 ):
     pass
 ```
diff --git a/crates/ruff_python_formatter/tests/snapshots/format@parentheses__expression_parentheses_comments.py.snap b/crates/ruff_python_formatter/tests/snapshots/format@parentheses__expression_parentheses_comments.py.snap
index 4a145d5e70..5e8e826231 100644
--- a/crates/ruff_python_formatter/tests/snapshots/format@parentheses__expression_parentheses_comments.py.snap
+++ b/crates/ruff_python_formatter/tests/snapshots/format@parentheses__expression_parentheses_comments.py.snap
@@ -1,6 +1,7 @@
 ---
 source: crates/ruff_python_formatter/tests/fixtures.rs
 input_file: crates/ruff_python_formatter/resources/test/fixtures/ruff/parentheses/expression_parentheses_comments.py
+snapshot_kind: text
 ---
 ## Input
 ```python
@@ -178,13 +179,13 @@ nested_parentheses4 = [
 
 x = (
     # unary comment
-    not # in-between comment
-    (
+    # in-between comment
+    not (
         # leading inner
         "a"
     ),
-    not # in-between comment
-    (
+    # in-between comment
+    not (
         # leading inner
         "b"
     ),
@@ -193,8 +194,8 @@ x = (
         "c"
     ),
     # 1
-    not # 2
-    (  # 3
+    # 2
+    not (  # 3
         # 4
         "d"
     ),
@@ -202,8 +203,8 @@ x = (
 
 if (
     # unary comment
-    not # in-between comment
-    (
+    # in-between comment
+    not (
         # leading inner
         1
     )