Prior to my recent purchase of a SanDisk Clip Sport, I enjoyed using a few iPod & iPad devices from Apple along with music file management with iTunes software. Even now, I continue to use iTunes to rip my CD collection into mp3 files for playback on my Clip Sport.
I always observed that iTunes automatically creates 2-digit prefixes to CD music filenames during the “ripping” process. These 2 digit prefix filenames are perfectly compatible with the FOLDER playback method of Clip Sport and Clip Jam.
Unfortunately, iTunes uses 1-digit track numbers in the ID3 tags for tracks 1-9 during the CD ripping process. The Clip Sport and Clip Jam will confuse the play order of music files using MUSIC playback method for 1-digit track numbers. One easy fix for this confusing behavior is to create 2-digit track numbers in the ID3 tags for music files 1- 9 (01, 02, 03, etc).
Once I decided I really enjoy using my cute little Clip Sport(s), using MUSIC playback mode, I decided I could easily resolve this minor nuisance using free mp3tag software. This software includes a command to change 1-digit track numbers to 2-digit numbers. Here is a link to the latest version (Jan. 2016).