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Jun 18, 2016 5:30 AM in response to zrowgzby turingtest2,When syncing isn't working properly the following steps should help, assuming all of the content you want is in your library.
(If it isn't see Recover your iTunes library from your iPod or iOS device.)
- Backup device.
- Restore as a new device.
- Restore the backup you made earlier.
tt2