I have been having this problem for about 6 months. I like to listen to the entire contents of my empeg (about 7600 songs) on random. When I load the entire contents it will work when I first try. The problem is the next time it boots up, it shows:

"End of playlist"
" (that's the pause icon)
0:00
[-/-]s

any ideas?
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50 Gig MK2 feat. over 7445 songs, 865 albums by 400 artists for 25 days of easy listening