Hi There, I have a 160 GB iPod classic, purchased back in 2007. Every time I sync, it starts syncing fine, but whenever it syncs somewhere past 33.5 GB iTunes gives me an error "attempting to copy to the Disk "IPOD"failed. An unknown error occurred (-69) and Windows prompts "Please insert a disk into IPOD (F" After a week of troubleshooting, I know it is not my library or songs on it (tried syncing with different computers and diferrent songs, plus my iPhone 4 syncs fine), not USB cable, not the computer. Has the iPod's time finally come? I made a playlist under 33 GB and can use it fine this way, however, that's like 20% of its capacity, which I used to have almost full, any ideas? Is the HDD finally dead? Probably bad controller on the iPod or something? Any way to fix it? Only way to bring the iPod back after this is to restore it, but everytime it gets to the same mark it happens again. Many thanks for your help!