Abstract: A portable digital media playback apparatus is preloaded with digital media files for preview. The files may be tagged with information to indicate the user wishes to purchase the digital media file or purchase certain digital rights associated with the digital media file. When the portable device is re-synched with a library of digital media files available for purchase, the files designated for purchase are downloaded to the portable device. In one embodiment, a user profile is created and includes a record of user events relating to the digital media files previewed, deleted or purchased. The content provider adopts a set of criteria for matches and creates a list of additional digital media files that are compatible with the user and which will be pushed down to the portable device the next time that the user synchronizes the device.