Embodiments of the invention provide a computer readable medium having computer executable instructions for synchronizing files between at least two portable media devices. A connection is established between one of at least two portable media devices and a portable synchronization device. A synchronization manager is initiated comprising predetermined instructions for synchronizing portable media devices. Based upon the instructions of the synchronization manager, and without requesting real-time user input, a determination is made whether to copy a file on the one of the at least two portable media devices. The file is ultimately transferred to another of the at least two portable media devices if the synchronization manager determines that the file should be transferred. A method is also provided comprising these steps. A portable media synchronization device is also provided for synchronizing at least two portable media devices.