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Oct 4, 2014 4:31 PM in response to matobiiby kcuttsjr81,Here's what worked for me. I've had this issue a few times, between iOS 6-8 and iPhone 5S to 6 (just today with the new phone).
FIRST - BACKUP FIRST
- Make sure your iPhone/iPad/iPod is backed up using iTunes. Use the cord (not WIFI).
- Be sure to "Transfer Purchases" as well.
- Sync and backup the device.
NEXT - FIX MUSIC SYNCING ISSUES
- Now, in iTunes, highlight the device, click the "Music" tab, and uncheck (click to uncheck) the "Sync Music" check box.
- Sync again.
- Then, turn off the device and restart it.
- Also close iTunes and restart the computer.
- When everything is ready, open iTunes and Sync the device again.
- After this time, highlight the device in iTunes, click the "Music" tab, and check (click to check) the "Sync Music" check box.
- Uncheck all of the previous music items in the list below the check box. Try only one playlist, artist, or album in the beginning.
- Sync again and you'll see it works.
Hope this works for you!