I don't know the answer to this and I'm still playing with my audio after just a week of taking delivery - but here is what I think might be going on. I have also copied quite a bit of music from iTunes on a USB memory stick. I've done this simply by dragging the tracks I want from iTunes to the stick (rather than whole playlists). When checking that all tracks have been copied to the stick I noticed that the song titles begin with a two-digit number that corresponds to the track number on the album (01, 02 etc.). I think that now I've transferred them to the Mini hard drive the songs are all listed this way, by track number - all the 01 tracks first, then the 02s and so on (and songs with the same track number listed alphabetically). I actually quite liked the resulting playlist - not 'random' exactly, but chopping and changing between albums. Not sure if I'm right about the way the hard drive is organising the music files, but this is how it looks to me. I'm sure someone will let me know if I'm wrong! Incidentally, I only discovered yesterday how to actually select "random" playback: it's in play options, which I think you get to by toggling right to options in play mode, then checking / unchecking the "random" box.