So, a radical edit, since I'm still having issues, and it's NOT the upgrade process, it's just the sync process.

Anyways, when I sync my phone to iTunes, a lot of my song files disappear from my phone. The songs appear to be on the phone, the playlist has items, even album artwork. It seems all the metadata is still there. Just the actual songs are missing. Trying to play most anything just fails with a missing song icon on the device as it quickly skips most files in the playlist. Files from iTunes itself do have the files deleted from the device, but then these are streamable files, so I actually get to play something as they stream from iTunes. The iTunes bought files still show up as not on the device though.

Another, probably related, oddity is the total unreliability of the free space indicator in iTunes. I can delete playlists from the sync, and free space goes down. I have the same rough group of playlists selected for sync, and free space varies by as much as +/- 4Gb.

So, most playlists lose all songs from device, and only streamable songs (read: bought from iTunes) get played. Individual Manually Added Songs are lost as well. To fix this, besides the turning on and off of music sync, on and off of playlists to sync, I tried a device restore, and it helped on the one sync, now the files are gone again. The upgrade to 8.0.2 didn't do much (thought helped battery life a bit).

5s + 8.0.2, Mavericks + iTunes 11.4

  • as you know apple servers are busy this days, so some patience is required.
    – Ruskes
    Commented Sep 23, 2014 at 1:37
  • @Buscar웃 I don't quite get your comment.. I have the latest iOS and iTunes, it's their interaction that's bad. How is the Apple download server interacting? Commented Sep 23, 2014 at 2:32
  • wouldn't the iTunes go out to check your library ?
    – Ruskes
    Commented Sep 23, 2014 at 2:36
  • Having exactly the same issues and have yet to resolve. Hard resets on the 6. Tried wiping and reinstalling all from iTunes backup and no joy. Please post any solutions you discover.
    – user93354
    Commented Oct 3, 2014 at 2:24
  • @user93354 finally got it fixed. Commented Oct 24, 2014 at 2:16

3 Answers 3


I had this problem and was able to resolve it by following the clues here: http://robservatory.com/a-nasty-little-itunesios-bug-may-be-causing-media-sync-issues/

Apparently it's a bug triggered by duplicates in the iTunes Library. In my case, I had a couple of duplicates that I wasn't aware of from several years ago.

I used the "Dupin" utility to find the duplicates. I eliminated the extra copies. I then turned off "Sync Music" in iTunes and did a sync. There was still some remnant music, so I went into Settings on the iPhone, then General > Usage > Manage Storage > Music. Click Edit and delete All Songs. The Settings app will probably crash but the music will be gone finally. Verify this in the Music app. Then turn on "Sync Music" in iTunes and resync.

  • Thanks much for this. Unfortunately I don't have a lot of time to check this on this week. Since this is a bug, and one Apple is aware of, I'm hoping this will be addressed in the iTunes update coming up with Yosemite this week. If it doesn't, I'll follow this advice. Commented Oct 13, 2014 at 21:43
  • I was switching between iCloud/iTunes Match and manually adding playlists, and had problems with music not appearing until I deleted the music and did a re-sync, and it fixed it. Commented Nov 23, 2014 at 0:15

I had the same problem on my iPhone 6 Plus running iOS 8.1 using iTunes 64-bit.

Following the advise of the accepted solution here resolved my issue: https://discussions.apple.com/thread/6545479

  1. On the device:
    1a. Open the "Settings" app
    1b. Tap on "General"
    1c. Tap on "Usage"
    1d. Tap on "Manage Storage" under "Storage" (not "iCloud")
    1e. Tap on "Music"
    1f. Tap on "Edit"
    1g. Tap on the new red circle to the left of "All Songs"
    1h. Tap on the new red "Delete" button to the right of "All Songs"
  2. In iTunes:
    2a. Open your device
    2b. Click on the "Music" tab under "Settings" of the device
    2c. Uncheck "Sync Music"
    2d. Sync your device
    2e. Check "Sync Music"
    2f. Sync your device
  • Glad that this worked for you, but I pretty much did this and it didn't work for me. Maybe 8.1 fixed this, but I did need to de-dupe Commented Nov 7, 2014 at 0:09


Finally got things to work. It was as @BillLipa said; a duplication of purchased songs (to add insult, it was the damn U2 album that somehow got downloaded twice).

My thing to add:

I didn't feel like paying for a de-dup tool, since the only reason i needed it was because of an Apple bug. So, I went into iTunes, looked at my device, and specifically music on my phone. Most songs were marked as missing, the only ones on the device were some of the purchased ones. I don't have a lot of purchased, so it was quick to track down what was both purchased and on the phone, and if it had a double. Six songs down the list was U2. Grrr... delete and resync. Music!

  • You're right, the issue does seem to be caused by dupes in the iPhone's music DB. And I concur that this appears to be caused by allowing the iPhone to automatically download purchases; when re-syncing with iTunes it results in dupes. Conclusion: turn off automatic music download under General->iTunes & App Store. In order to fix this, I had to tick "manually manage music" in iTunes, then manually delete the dupes and suddenly over 1250 songs that were missing from my iPhone got sync'ed. What a nasty (and pretty obvious) bug...
    – sxc731
    Commented Nov 24, 2014 at 15:09
  • Spoke a too soon. Although I manually deleted the duplicate songs from my iPhone (first individually, then the whole album in which they appear), as soon as I set the iPhone to sync with iTunes again, the ghost double entries re-appear... sigh... Still can't believe Apple can be satisfied with such nasty bugs plaguing its users for such a long time (this one's been there at least since iOS7)
    – sxc731
    Commented Nov 24, 2014 at 21:21

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