Your iPod software can be out of date. All you have to do is to select restore iPod to factory defaults either in the iTunes program or on the iPod itself. This will restore the iPod to the original factory condition. A word of caution is that you will loose all of your songs as they will be erased. If your iPod is still not syncing with iTunes on your PC or mac, then I suggest rebooting both the PC and iPod with the usb plug disconnected. Once the PC is back on and completely booted up, plug in the usb cord on the iPod and iTunes should pop up and you should be able to sync your iPod to iTunes Try to reboot the iPod and PC a few times if necessary, it should work.