sigh You're not "LOCKED" into using iTunes. Yes, it is terrible software. I've used it a grand total of one time, when I first got my iPod classic a few years ago, in order to initialize/name it. Ever since then, I've been managing it with other software. I use Amarok on Linux, and for Windows, I use Winamp. You just plug the iPod in and it comes right up under Portable Devices, and you can copy to and from it flawlessly, including album art and everything. So many people think they're forced to use iTunes or see it as being somehow connected with the iPod, but a simple google search will return a plethora of alternatives that are more than a complete replacement of iTunes.