diff --git a/crates/ruff_python_formatter/resources/test/fixtures/ruff/expression/attribute.py b/crates/ruff_python_formatter/resources/test/fixtures/ruff/expression/attribute.py
index 6f5a7ac1a6..a760491b3d 100644
--- a/crates/ruff_python_formatter/resources/test/fixtures/ruff/expression/attribute.py
+++ b/crates/ruff_python_formatter/resources/test/fixtures/ruff/expression/attribute.py
@@ -169,3 +169,53 @@ result = (
     # dangling before dot
     .b # trailing end-of-line
 )
+
+# Regression test for https://github.com/astral-sh/ruff/issues/19350
+variable = (
+    (something)  # a comment
+    .first_method("some string")
+)
+
+variable = (
+    something # a commentdddddddddddddddddddddddddddddd
+    .first_method("some string")
+)
+
+if (
+    (something)  # a commentdddddddddddddddddddddddddddddd
+    .first_method("some string")
+): pass
+
+variable = (
+    (something # a comment
+    ).first_method("some string")
+)
+
+if (
+    (something # a comment
+    ).first_method("some string") # second comment
+): pass
+
+variable = ( # 1
+    # 2
+    (something)  # 3
+    # 4
+    .first_method("some string") # 5
+    # 6
+) # 7
+
+
+if (
+    (something
+    # trailing own line on value
+    )
+    .first_method("some string")
+): ...
+
+variable = (
+    (something
+    # 1
+    )  # 2
+    .first_method("some string")
+)
+
diff --git a/crates/ruff_python_formatter/src/expression/expr_attribute.rs b/crates/ruff_python_formatter/src/expression/expr_attribute.rs
index ebb0093ccb..781b8b4601 100644
--- a/crates/ruff_python_formatter/src/expression/expr_attribute.rs
+++ b/crates/ruff_python_formatter/src/expression/expr_attribute.rs
@@ -179,7 +179,22 @@ impl NeedsParentheses for ExprAttribute {
             context.comments().ranges(),
             context.source(),
         ) {
-            OptionalParentheses::Never
+            // We have to avoid creating syntax errors like
+            // ```python
+            // variable = (something) # trailing
+            // .my_attribute
+            // ```
+            // See https://github.com/astral-sh/ruff/issues/19350
+            if context
+                .comments()
+                .trailing(self.value.as_ref())
+                .iter()
+                .any(|comment| comment.line_position().is_end_of_line())
+            {
+                OptionalParentheses::Multiline
+            } else {
+                OptionalParentheses::Never
+            }
         } else {
             self.value.needs_parentheses(self.into(), context)
         }
diff --git a/crates/ruff_python_formatter/tests/snapshots/format@expression__attribute.py.snap b/crates/ruff_python_formatter/tests/snapshots/format@expression__attribute.py.snap
index 89ce7d237b..4677ca06de 100644
--- a/crates/ruff_python_formatter/tests/snapshots/format@expression__attribute.py.snap
+++ b/crates/ruff_python_formatter/tests/snapshots/format@expression__attribute.py.snap
@@ -175,6 +175,56 @@ result = (
     # dangling before dot
     .b # trailing end-of-line
 )
+
+# Regression test for https://github.com/astral-sh/ruff/issues/19350
+variable = (
+    (something)  # a comment
+    .first_method("some string")
+)
+
+variable = (
+    something # a commentdddddddddddddddddddddddddddddd
+    .first_method("some string")
+)
+
+if (
+    (something)  # a commentdddddddddddddddddddddddddddddd
+    .first_method("some string")
+): pass
+
+variable = (
+    (something # a comment
+    ).first_method("some string")
+)
+
+if (
+    (something # a comment
+    ).first_method("some string") # second comment
+): pass
+
+variable = ( # 1
+    # 2
+    (something)  # 3
+    # 4
+    .first_method("some string") # 5
+    # 6
+) # 7
+
+
+if (
+    (something
+    # trailing own line on value
+    )
+    .first_method("some string")
+): ...
+
+variable = (
+    (something
+    # 1
+    )  # 2
+    .first_method("some string")
+)
+
 ```
 
 ## Output
@@ -328,4 +378,54 @@ result = (
     # dangling before dot
     .b  # trailing end-of-line
 )
+
+# Regression test for https://github.com/astral-sh/ruff/issues/19350
+variable = (
+    (something)  # a comment
+    .first_method("some string")
+)
+
+variable = something.first_method(  # a commentdddddddddddddddddddddddddddddd
+    "some string"
+)
+
+if (
+    (something)  # a commentdddddddddddddddddddddddddddddd
+    .first_method("some string")
+):
+    pass
+
+variable = (
+    something  # a comment
+).first_method("some string")
+
+if (
+    (
+        something  # a comment
+    ).first_method("some string")  # second comment
+):
+    pass
+
+variable = (  # 1
+    # 2
+    (something)  # 3
+    # 4
+    .first_method("some string")  # 5
+    # 6
+)  # 7
+
+
+if (
+    something
+    # trailing own line on value
+).first_method("some string"):
+    ...
+
+variable = (
+    (
+        something
+        # 1
+    )  # 2
+    .first_method("some string")
+)
 ```