diff --git a/crates/ruff_python_parser/resources/invalid/re_lex_logical_token.py b/crates/ruff_python_parser/resources/invalid/re_lex_logical_token.py
index 86e2b1435bd19..9a2b9f4fb3500 100644
--- a/crates/ruff_python_parser/resources/invalid/re_lex_logical_token.py
+++ b/crates/ruff_python_parser/resources/invalid/re_lex_logical_token.py
@@ -54,4 +54,10 @@ def bar():
 
 if call(f"hello
     def bar():
-        pass
\ No newline at end of file
+        pass
+
+
+# There are trailing whitespace before the newline character but those whitespaces are
+# part of the comment token
+f"""hello {x # comment    
+y = 1
\ No newline at end of file
diff --git a/crates/ruff_python_parser/src/lexer.rs b/crates/ruff_python_parser/src/lexer.rs
index 0decf4cb804d0..c4a44b106d8eb 100644
--- a/crates/ruff_python_parser/src/lexer.rs
+++ b/crates/ruff_python_parser/src/lexer.rs
@@ -1370,17 +1370,16 @@ impl<'src> Lexer<'src> {
         // i.e., it recovered from an unclosed parenthesis (`(`, `[`, or `{`).
         self.nesting -= 1;
 
-        let current_position = self.current_range().start();
+        let mut current_position = self.current_range().start();
         let reverse_chars = self.source[..current_position.to_usize()].chars().rev();
-        let mut new_position = current_position;
-        let mut has_newline = false;
+        let mut newline_position = None;
 
         for ch in reverse_chars {
             if is_python_whitespace(ch) {
-                new_position -= ch.text_len();
+                current_position -= ch.text_len();
             } else if matches!(ch, '\n' | '\r') {
-                has_newline |= true;
-                new_position -= ch.text_len();
+                current_position -= ch.text_len();
+                newline_position = Some(current_position);
             } else {
                 break;
             }
@@ -1388,7 +1387,7 @@ impl<'src> Lexer<'src> {
 
         // The lexer should only be moved if there's a newline character which needs to be
         // re-lexed.
-        if new_position != current_position && has_newline {
+        if let Some(newline_position) = newline_position {
             // Earlier we reduced the nesting level unconditionally. Now that we know the lexer's
             // position is going to be moved back, the lexer needs to be put back into a
             // parenthesized context if the current token is a closing parenthesis.
@@ -1410,7 +1409,7 @@ impl<'src> Lexer<'src> {
             }
 
             self.cursor = Cursor::new(self.source);
-            self.cursor.skip_bytes(new_position.to_usize());
+            self.cursor.skip_bytes(newline_position.to_usize());
             self.state = State::Other;
             self.next_token();
             true
diff --git a/crates/ruff_python_parser/tests/snapshots/invalid_syntax@re_lex_logical_token.py.snap b/crates/ruff_python_parser/tests/snapshots/invalid_syntax@re_lex_logical_token.py.snap
index 2a3c1866e7999..7604d4bede3ee 100644
--- a/crates/ruff_python_parser/tests/snapshots/invalid_syntax@re_lex_logical_token.py.snap
+++ b/crates/ruff_python_parser/tests/snapshots/invalid_syntax@re_lex_logical_token.py.snap
@@ -7,7 +7,7 @@ input_file: crates/ruff_python_parser/resources/invalid/re_lex_logical_token.py
 ```
 Module(
     ModModule {
-        range: 0..979,
+        range: 0..1129,
         body: [
             If(
                 StmtIf {
@@ -670,6 +670,53 @@ Module(
                     ],
                 },
             ),
+            Expr(
+                StmtExpr {
+                    range: 1097..1109,
+                    value: FString(
+                        ExprFString {
+                            range: 1097..1109,
+                            value: FStringValue {
+                                inner: Single(
+                                    FString(
+                                        FString {
+                                            range: 1097..1109,
+                                            elements: [
+                                                Literal(
+                                                    FStringLiteralElement {
+                                                        range: 1101..1107,
+                                                        value: "hello ",
+                                                    },
+                                                ),
+                                                Expression(
+                                                    FStringExpressionElement {
+                                                        range: 1107..1109,
+                                                        expression: Name(
+                                                            ExprName {
+                                                                range: 1108..1109,
+                                                                id: "x",
+                                                                ctx: Load,
+                                                            },
+                                                        ),
+                                                        debug_text: None,
+                                                        conversion: None,
+                                                        format_spec: None,
+                                                    },
+                                                ),
+                                            ],
+                                            flags: FStringFlags {
+                                                quote_style: Double,
+                                                prefix: Regular,
+                                                triple_quoted: true,
+                                            },
+                                        },
+                                    ),
+                                ),
+                            },
+                        },
+                    ),
+                },
+            ),
         ],
     },
 )
@@ -831,8 +878,45 @@ Module(
 
 
    |
-55 | if call(f"hello
-56 |     def bar():
-57 |         pass
-   |              Syntax Error: Expected a statement
+60 | # There are trailing whitespace before the newline character but those whitespaces are
+61 | # part of the comment token
+62 | f"""hello {x # comment    
+   |  Syntax Error: Expected a statement
+63 | y = 1
+   |
+
+
+   |
+60 |   # There are trailing whitespace before the newline character but those whitespaces are
+61 |   # part of the comment token
+62 |   f"""hello {x # comment    
+   |  ___________________________^
+63 | | y = 1
+   | |_____^ Syntax Error: f-string: unterminated triple-quoted string
+   |
+
+
+   |
+61 | # part of the comment token
+62 | f"""hello {x # comment    
+63 | y = 1
+   | ^ Syntax Error: f-string: expecting '}'
+   |
+
+
+   |
+60 |   # There are trailing whitespace before the newline character but those whitespaces are
+61 |   # part of the comment token
+62 |   f"""hello {x # comment    
+   |  ___________________________^
+63 | | y = 1
+   | |_____^ Syntax Error: Expected FStringEnd, found Unknown
+   |
+
+
+   |
+61 | # part of the comment token
+62 | f"""hello {x # comment    
+63 | y = 1
+   |       Syntax Error: Expected a statement
    |