A digital audio playback device that includes a wireless communication link to enable it to interact and synchronize with computing platforms as well as other mobile digital audio players and fixed digital audio players. A digital audio playback device is configured such that the computing platform may automatically or upon user request copy, add or remove digital audio content or other information, such as playlists. In addition, digital content on the digital audio playback device can be synchronized with a computing platform. In one embodiment of the invention, the digital audio playback device is configured to enable wireless communication among other digital playback devices and/or a computing platform to allow synchronization and control.