A content management system rendering a file sharing GUI on a first device which is communicatively coupled to a content management system and associated with a first user having an account with the content management system. A file to be shared with a second user is identified in response to the file being selected and dragged. In response to the file being identified, a contact section displaying contact icons is rendered. The selected file is released on a displayed contact icon and a user identifier, e.g., an email address or account, associated with the displayed contact icon is identified. In response to the user identifier being identified, the selected file is shared with a second user associated with the user identified.