diff --git a/crates/ruff_python_formatter/src/comments/placement.rs b/crates/ruff_python_formatter/src/comments/placement.rs
index 234752ba53..d0906d24b6 100644
--- a/crates/ruff_python_formatter/src/comments/placement.rs
+++ b/crates/ruff_python_formatter/src/comments/placement.rs
@@ -1865,7 +1865,7 @@ fn handle_unary_op_comment<'a>(
         .find(|token| token.kind == SimpleTokenKind::LParen)
         .map_or(unary_op.operand.start(), |lparen| lparen.start());
     if comment.end() < up_to {
-        CommentPlacement::leading(unary_op, comment)
+        CommentPlacement::leading(&*unary_op.operand, 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 67f54f9da9..2cdde4e0d9 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
@@ -1,7 +1,6 @@
 ---
 source: crates/ruff_python_formatter/tests/fixtures.rs
 input_file: crates/ruff_python_formatter/resources/test/fixtures/ruff/expression/unary.py
-snapshot_kind: text
 ---
 ## Input
 ```python
@@ -200,6 +199,11 @@ def foo():
         not (aaaaaaaaaaaaaaaaaaaaa[bbbbbbbb, ccccccc]) and dddddddddd < eeeeeeeeeeeeeee
     ):
         pass
+
+# Regression test for https://github.com/astral-sh/ruff/issues/19226
+if '' and (not #
+0):
+    pass
 ```
 
 ## Output
@@ -250,31 +254,35 @@ if +(
     pass
 
 if (
+    not
     # comment
-    not aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa
+    aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa
     + bbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbb
 ):
     pass
 
 
 if (
+    ~
     # comment
-    ~aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa
+    aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa
     + bbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbb
 ):
     pass
 
 if (
+    -
     # comment
-    -aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa
+    aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa
     + bbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbb
 ):
     pass
 
 
 if (
+    +
     # comment
-    +aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa
+    aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa
     + bbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbb
 ):
     pass
@@ -283,8 +291,8 @@ if (
 
 if (
     # unary comment
-    # operand comment
-    not (
+    not # operand comment
+    (
         # comment
         aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa
         + bbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbb
@@ -318,31 +326,36 @@ if (
 
 ## Trailing operator comments
 
-if (  # comment
-    not aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa
+if (
+    not
+    # comment
+    aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa
     + bbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbb
 ):
     pass
 
 
 if (
+    ~
     # comment
-    ~aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa
+    aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa
     + bbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbb
 ):
     pass
 
 if (
+    -
     # comment
-    -aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa
+    aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa
     + bbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbb
 ):
     pass
 
 
 if (
+    +
     # comment
-    +aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa
+    aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa
     + bbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbb
 ):
     pass
@@ -362,13 +375,16 @@ if (
     pass
 
 if (
+    not
     # comment
-    not a
+    a
 ):
     pass
 
-if (  # comment
-    not a
+if (
+    not
+    # comment
+    a
 ):
     pass
 
@@ -385,9 +401,9 @@ if True:
 # Regression test for: https://github.com/astral-sh/ruff/issues/7448
 x = (
     # a
-    # b
+    not # b
     # c
-    not (  # d
+    (  # d
         # e
         True
     )
@@ -415,4 +431,13 @@ def foo():
         not (aaaaaaaaaaaaaaaaaaaaa[bbbbbbbb, ccccccc]) and dddddddddd < eeeeeeeeeeeeeee
     ):
         pass
+
+
+# Regression test for https://github.com/astral-sh/ruff/issues/19226
+if "" and (
+    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 5e8e826231..4a145d5e70 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
@@ -1,7 +1,6 @@
 ---
 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
@@ -179,13 +178,13 @@ nested_parentheses4 = [
 
 x = (
     # unary comment
-    # in-between comment
-    not (
+    not # in-between comment
+    (
         # leading inner
         "a"
     ),
-    # in-between comment
-    not (
+    not # in-between comment
+    (
         # leading inner
         "b"
     ),
@@ -194,8 +193,8 @@ x = (
         "c"
     ),
     # 1
-    # 2
-    not (  # 3
+    not # 2
+    (  # 3
         # 4
         "d"
     ),
@@ -203,8 +202,8 @@ x = (
 
 if (
     # unary comment
-    # in-between comment
-    not (
+    not # in-between comment
+    (
         # leading inner
         1
     )