Automatic download of personalized media content to a portable media device based on user preferences is disclosed. A media service can evaluate content on a user's media device as well as user action related thereto to infer the user's preferences, and can automatically aggregate and download content that is relevant to the user's tastes. The user can subscribe to, for example, playlists generated by the media service, another user's playlist(s), a simulated radio station, etc., and can receive content updates thereto at predefined intervals and/or upon release of the updates. In this manner, the user can periodically receive media content that is personalized to the user without requiring the user to explicitly request the content or synchronize to a PC.