In a content supply system, content data is supplied from a content supply apparatus to a content playback apparatus via a network. The content playback apparatus includes a request device for requesting a recovery process; an obtaining device for obtaining a start-up file; and a download device for downloading the content data. The content supply apparatus includes a customer information management device for managing customer information; a notification device for notifying the recovery information to the content playback apparatus; a start-up file generation device for generating a start-up file; a storage device for storing the start-up file; a content data supply device for allowing the content data to be downloaded; and a license data supply device for allowing the license data to be downloaded.