Abstract: System and methods for managing content on a media device such as a portable digital audio device are described. The system recognizes when a digital audio device is connected to a computer and it automatically notifies a user that the audio device is connected and provides an entry point through which content of the audio device can be managed. The audio device is presented in an extended namespace (UI extension) of an operating system user interface in the same manner that typical storage devices (e.g., hard drives and floppy drives) are presented by the operating system user interface. Contents (e.g., music files) of the audio device are manageable through the UI extension in the same familiar manner as the contents of other typical storage devices of the computer.