A method, system and computer program provide a mechanism for intelligently synchronizing a portable video device with a digital video recorder. The intelligent synchronization handles conditions under which a complete transfer of difference content is not possible due to available storage limitations of the portable video device. The synchronization process determines a content difference between the content on the portable video device and the content on the DVR, determines available storage space on the portable video device and compares the available storage space on the portable video device to a size of the content difference. If the size of the content difference is greater than the available storage space, the size of the content difference is reduced, by compression or truncation, without completely excluding video programs from the transfer.