Setup: Windows 10 64-bit, iTunes 12.7.0.166, iPod Classic 160Gb. I have several gigabytes of music, podcasts and audiobooks in iTunes, all of which I have been syncing to the Classic for years, without problems.
I now have a new Touch 128Gb (iOS 10.3.1). I have tried several times to sync everything* to this device, but without success. iTunes shows that it is copying many items for a long time and then "finishes", but it seems that nothing or only a few gigabytes have been copied. If I try to sync again, I sometimes get an error message about failing to start the sync.
I am now updating the Touch to iOS 11 in the hopes that this will fix it.
What else could I try?
*I have selected to sync all music, all episodes of all podcasts and all audiobooks.
Best Answer
I would sync one album or one playlist. That lets you know everything is fine on the overall OS and hardware connection level.
From there, add or subtract tracks to sync until you locate the problematic ones that cause the sync to fail.