Hi there, I have a Macbook pro running the latest version of OSX, and iTunes version 8.2. I have an iPod Classic, 80GB, that is about 1.5 - 2 years old. I had the hard drive replaced about 1 year ago because it crashed. I also have an obsession with Jeff Buckley, but my iPod clearly disapproves. I ripped one of his CDs into my iTunes at the 256kb (VBR) rate, 44.1khz. I plugged in my iPod, and it synched. However, the Buckley songs were not copied across. I opted to manually manage music, emptied my iPod, and dragged all the songs across. Everything appears to be there, except the Jeff Buckley. I reset my iPod, and tried again - still no dice. I reset it again, and tried again. This time, I checked the "music" tab under my iPod from within iTunes - and hello, there's the Buckley. I can even play it from there. However, I disconnect my iPod, and he disappears. WTF? Any assistance would be greatly appreciated.