I once knew how to do this, but after having not done it in 10 or 12 years, I can't seem to crack the code. My device is running fine, and iTunes detects it through Windows no problem. I ripped a couple discs to iTunes but can't get the files to my device. I also seem to remember when ripping a disc, in Advanced I would be asked if I wanted the files to go to computer hard drive or to iPod, which was my preference...but I can't quite seem to get there...