I couldn't delete tracks at all with MC13 when running it on WinXP, but can now do it just fine with Win7, which is an oddity, but one I'm grateful for (yes, I know I should upgrate to MC14, but I am fed up with MC support again and am not ready to give them any more money). I gave up on the "delete files from handheld..." option a long time ago, and haven't even tried it with Win7. Things work pretty OK for now and I don't want to mess them up. I reformatted my Zen maybe three weeks ago and on the second sync after reloading everything there were duplicate tracks. The thing is impossible. It's durable, cute, handy, reasonably reliable, has good battery life, and fun, but can be downright contrary sometimes. I'm still tempted to get another, larger Zen, but just got a phone with wicked battery life, so my problems may be solved.