Abstract: A system and a method are disclosed for media file management, e.g., on a handheld computing device. The media file management system includes detecting presence of a storage media from a media device and automatically invoking software particularly configured to manipulate media files (or data) on the detected storage media. The media management system also includes detecting duplicate media files for transfer from a first location to a second location and in response to such detection of duplicates, stopping (or preventing) transfer of such duplicative media file. In addition, the media management system is configured to emulate on the handheld computing device a directory and file structure corresponding to particular media standards to allow existing media application software on a host computing system access the media files on the handheld computing device as an extension of the host computing system.