Got an older 20GB iPod. Also, got the same desktop that I originally set up my iTunes/iPod on. Never switched computers. I haven't sync'd my iPod in several months. Just imported new CD's into my iTunes library on my desktop. I plug in my iPod expecting it to AUTOSYNC just like a million times before. But nothing. I go to "File" menu to manually select "Sync iPod", but dammit "Sync iPod" is grayed out, can't choose it. It's like iTunes doesn't recognize the iPod is hooked up. I really don't think it's a hardware problem (meaning the cable) b/c my iPod is charging when I hook it up. Any ideas? I don't remember for certain, but I may have downloaded an iTunes update since I last sync'd. Possible that is causing a problem?