The present invention discloses a system and method for synchronizing data between a first data store and a second data store. The system can include a synchronization component, a compression pre-processor, and a compression/decompression component. The synchronization component can automatically synchronize content between the first data store and the second data store. The compression pre-processor can determine a compression ratio for digital content before the digital content is compressed. The compression/decompression component can selectively compress digital content based upon the compression ratio determined by the compression pre-processor. The selectively compressed digital content can be automatically conveyed between the first data store and the second data store during synchronization operations involving the synchronization component. The compression/decompression component can automatically decompress received content that has been compressed. This decompression can occur automatically before adding the digital content to a content receiving data store.