I have this same problem, which is why I had to through all my itunes onto my windows running laptop, how old is your mac and what OS are you running? Mine is 5 years old and runs 10.4.11, and my I pod is only compatible with OS 10.5.something. basically you either need to buy a new OS, or a new mac, or run your thing on windows (not a fun thing, it cant find album art for stuff I bought off the itunes store)