Well, I'm used to using Winamp on my PC, typically all my mp3's are just in a big folder and I let Winamp use random play (which incidentally is really random), I'll see how good the Sony random play is, I heard some mp3 players aren't that "random" if you know what I mean. My mp3's are sensibly named with Artist - Song Title as the filename so I never had a need for id3 before which probably sounds weird to most people... Now here are some observations about the mp3 file manager software. I gues the id3 tag thing may be relevant because I have some REALLY weird names on the display of the player for some songs and a lot of "aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa" or "------------------------------" showing as the artist, or album or group. There doesn't appear to be any particular reason for this, because some (as I had expected) show up with the filename intact, and in the "Untitled" folder. The software as you said was basic but works ok, although some mp3's it just refused to load up, the most mp3's I could load into it in one go was 53 and it took a while. I'd suspect it was the software itself as the bottleneck as I'm on USB 2.0 with a 3Ghz P4 with 1 gig of RAM. I don't know if the Sony MP3 filemanger software has a preference for a certain type of encoding and that's why it baulked at some mp3's but if memory serves me correctly, most are 192 kbps and are either LAME, BladeEnc, or Fraunhofer encoded I don't know how I would go about inspecting a mp3 to see how it was encoded.