A collaborative content management system enables users to selectively create file-level comments, in addition to content level comments, in collaborative content items. A file-level comment can be created in a number of different ways, including creating a comment associated with a title, header, heading, or other designated portion of the content; by designating a message associated with sharing the content item as a file-level comment; by replaying via a messaging system to a message sharing the content item; or by including a file-level primitive in the content of a comment. A file-level comment may be indicated in the collaborative content item by visually distinguishing formatting of a title, header or other portion of the content item. A file-level comment may be displayed in a visually distinctive manner, such as with specified formatting or in a specific window pane apart from content level comments.