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Itunes Sync messed up artwork and music

I synced my itunes to my phone from my computer, now all of the artwork is messed up (wrong artwork with wrong albums) and when I try to play some of the songs, they will skip over some of the songs, even though they should be there. There are also duplicates of the same song in my lists. I noticed this issue after I imported some CDs and then synced my phone. Really annoying. Leaving tomorrow on a long car ride and would love to be able to listen to my music without these annoying issues.


As a side note, I made sure to update my itunes and I have the most recent iOS on my iphone 8 Plus.

iPhone 8 Plus

Posted on Dec 20, 2018 8:39 AM

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Posted on Dec 20, 2018 4:41 PM

You could try the following all-purpose steps for dealing with erratic device or sync behaviour (including the troublesome greyed out tracks and/or dotted circles of stalled transfers). They assume that all of the content you want on the device is in your library ready for restoring. If it isn't see Recover your iTunes library from your iPod or iOS device first. I would also recommend you copy everything out of the camera roll if you haven't already.


  1. Backup device.
  2. Restore as a new device.
  3. Restore the backup you made earlier.


Use an encrypted backup (*) if you want to preserve passwords, Wi-Fi settings, web history and health data where appropriate. I also suggest syncing with a selection of playlists (unless you're using iCloud Music Library) rather than manually adding content as, if nothing else, the process above is easier to do if you ever have to go through it again.


(*) The downside with backup encryption is that if you forget the password when you need it again, which could be years later, you may need to invoke a workaround to turn off encryption as shown in Disable iOS backup encryption, which can only help if your device is in a state that can backup to iCloud, or runs iOS 11.



For added security you might also want to make an independent backup to iCloud and/or archive your current backup before you start.



FWIW I successfully used this method some time ago when Siri became unable to call contacts or play my music.



tt2

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1 reply
Question marked as Best reply

Dec 20, 2018 4:41 PM in response to totravel01

You could try the following all-purpose steps for dealing with erratic device or sync behaviour (including the troublesome greyed out tracks and/or dotted circles of stalled transfers). They assume that all of the content you want on the device is in your library ready for restoring. If it isn't see Recover your iTunes library from your iPod or iOS device first. I would also recommend you copy everything out of the camera roll if you haven't already.


  1. Backup device.
  2. Restore as a new device.
  3. Restore the backup you made earlier.


Use an encrypted backup (*) if you want to preserve passwords, Wi-Fi settings, web history and health data where appropriate. I also suggest syncing with a selection of playlists (unless you're using iCloud Music Library) rather than manually adding content as, if nothing else, the process above is easier to do if you ever have to go through it again.


(*) The downside with backup encryption is that if you forget the password when you need it again, which could be years later, you may need to invoke a workaround to turn off encryption as shown in Disable iOS backup encryption, which can only help if your device is in a state that can backup to iCloud, or runs iOS 11.



For added security you might also want to make an independent backup to iCloud and/or archive your current backup before you start.



FWIW I successfully used this method some time ago when Siri became unable to call contacts or play my music.



tt2

Itunes Sync messed up artwork and music

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