You can organize your music files to playback in the desired order by renaming the files in alphanumerical sequence such as 001_Drunken Monkey.mp3 followed by 002_Massachusetts.mp3 etc. prior to transferring them to the GoGear. If folders are being used, please also make sure that the folder names are in alphanumerical sequence according to your playback order. Tracks in the root directory will be playing first then the content of folders.