Back in the early days of iTunes, I bought an iPod Mini and synced it on a Windows machine. Occasionally, I would sync my iPod, and something like 20 songs woul

Back in the early days of iTunes, I bought an iPod Mini and synced it on a Windows machine. Occasionally, I would sync my iPod, and something like 20 songs would disappear (purchased and non-purchased). This happened without warning, with alarming frequency. This was a known bug as late as iTunes 7, which would sometimes disregard the "Automatic Media Folder Management" setting, do it anyways, and sometimes files/folders.