Techniques are disclosed herein for managing the transfer of digital media that is recorded on a source device (e.g., personal video recorder) to a target device (e.g., portable media player). In one aspect, a user interface is provided for scheduling recording of digital media content on a source device and for inputting user preferences for transferring digital media content to be recorded on the source device to a target device. A user request is received in the user interface to schedule recording of digital media on the source device. User preferences for transferring digital media from the source device to the target device are also received in the user interface. The digital media is recorded on the source device per the user's request. Synchronization of the recorded digital media from the source device to the target device is managed based on the user preferences.