iTunes keeps syncing the same 44 songs OVER and OVER: SOLVED!

iTunesRight as OS 3.0 came out  iTunesfor the iPhone and just after the latest version of iTunes was release a problem sprung up for me.  Without making any changes to any of my music files, iTunes would resync the same 44 songs to the iPhone on every sync.  I finally had some time to track it down.  Well, in truth, it finally annoyed me enough to find a fix.

It turns out the problems were broken id3 tags.  Now, if you ask me how they were broken, I honestly have no idea.  What I ended up doing is for mp3s that still had v1 tags, I removed the v1 tags.  My first thought was it was mp3s where v1 tags didn’t match v2 tags.  I used the excellent command line tool id3v2 to strip off the v1 tags, and then revisited the songs in iTunes information panel to make sure iTunes’s database matched what the songs now looked like.  Sync the iPhone, disconnect the iPhone, reconnect the iPhone, sync again, and boom, those files weren’t synced again.  Rinse and repeat until all were fixed until…

I ended up finding that a few of the 44 only had v2 tags, so it wasn’t the v1 tags alone.  On a whim I tried this fix which seemed to work: In iTunes I converted the v2 tags from say, version 2.3 to 2.2 and back, do the sync, rinse and repeat dance from above and that seemed to fix it.

On a related note, I found an excellent OS X only iTunes utility that does two very cool things I had been doing by hand: adding album art and lyrics.  Actually, I hadn’t been adding lyrics, but I’m considering it now that there is an easy way to do it.  The cool it called GimmieSomeTune.  What makes its album art gathering go above and beyond the iTunes’s native searching of the iTunes store is that if its not in the iTunes store, it’ll try to gather the album art from Amazon.  Amazon’s art has been hit and miss in terms of quality, but I prefer to have something there rather than the empty music symbol.  (You can also create your own default that will be put in place if iTunes can’t find it in either place.)  It also has some interesting features like integration, but I haven’t had a chance to play with that yet.

8 thoughts on “iTunes keeps syncing the same 44 songs OVER and OVER: SOLVED!”

  1. I’ve had this problem with 500 songs for months. I’ve run MP3 scanners on all my files and they all report as good. Upgrading the tags fixed it. Thank you!

  2. I’ve had this problem for quite a while now and it does it on my iPhone and my iPod.

    Using your post, I thought about the ID3 tag issue and came up with another method that fixes the problem because it, I presume, resets the tags on all the songs.

    I have iTunes 9 and OSX 10.6 and this worked for me:

    Select all the songs in your library,
    select get-info,
    select the options tab,
    select “remember the play position” and say *yes* to it,
    then apply the changes.

    Wait while iTunes changes every song in your library to this new option.

    Then, go through the same process to turn *Off* the same “remember the play position” option and wait while iTunes changes all songs back again.

    For me, this fixed the problem.


  3. It definitely has to do with the “Convert higher bit rate songs to 128 kbps AAC” option. I thought this sounded like a good idea so enabled it initially, however, this was causing my songs to be re-synced every single time I plugged in my iPhone. I’ve disabled this option, and now the problem is gone!

    1. I had this problem with iTunes before 9.1 and without the downsampling, so I had some other issue.

      If it crops up again, I’ll have to see if 9.1.1 fixes it.

      But I should update the top post to reflect this.

  4. From Apple Tech Support:

    If your songs with lyrics are re-syncing every time you sync (with 128 kbps conversion enabled) after updating to iTunes 9.1.1, follow these steps:
    1. Re-download the iTunes 9.1.1 installer from
    2. Run the installer.
    This will install iTunes over the existing
    3. Open iTunes.
    iTunes will automatically update your iTunes Library. This may take a while for large libraries, but after the update has completed, syncing should return to normal.

    -I have been looking for a fix to this problem for a while. I’ve had the same 39 songs resyncing every time I plugged my phone in. Yesterday due to another issue I backed my phone up, reset my phone to factory settings and then reloaded from the backup and then I had over 2,000 songs that resynced, not good.

    -I just Googled the problem and found this forum… how lucky am I that Mike Reeser answered this question in 2009. I just tried his suggestion and it worked like a charm. Thanks Mike… I’m sure you won’t see this since it’s so old, but you helped a user in need out. Much appreciated.

  6. Mike R., that worked for me. I had 54 songs from 6 different albums that kept resyncing, so I selected each album one by one, changed the remember position option to yes, OK’d the changes, and then changed them all back.

    Thanks Keith and Mike for posting your findings!

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