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A nasty little iTunes/iOS bug may be causing media sync issues

November 18th update: My sync issues returned, but due to a different cause this time. Details in this post.

After complaining to Tim Cook, and separately starting a (now closed) support ticket, it appears that my iOS/iTunes sync nightmare has finally come to an end!

I have not seen a progress bar that busy since the day I brought my iPhone 6 back home. Whatever I tried, iTunes simply would not sync everything in my library. In the end, the problem turned out to be as simple—but as deadly—as this:

In the current version of iTunes/iOS, there’s a bug that only appears when you have duplicates of purchased songs. When encountered, a duplicate of a purchased song will (almost always) cause iTunes to silently stop syncing.

This is a known-to-Apple issue, and it will be fixed in a forthcoming update. I’m fairly certain it’s an iTunes bug, but as Apple didn’t clearly state which it was, I’m calling it iTunes/iOS. Either way, until it’s fixed, it’s a really bad bug.

Here’s what happens: If you have duplicates of purchased songs, iTunes simply silently stops syncing when it hits one of those duplicates. From your perspective, it will look like everything is working—iTunes never throws an error, and it proceeds through all six (or seven or whatever) steps of the sync process, as seen in the status window of iTunes.

But behind the scenes, nothing is happening—at least, nothing relative to syncing your files. As seen by my troubles, this can be incredibly frustrating and hard to fix.

Continue reading to see how I was able to finally (with Apple’s help) get my devices syncing again—the tricky part is finding all the duplicates, because they’re not all obvious. Also note that if you are not having sync issues, I wouldn’t worry about duplicates—no need to endanger what’s already working well!

The “tell”

If you’re affected by this bug, you’ll find that your iOS device will get some, but not all, of your content. When you look at the device in iTunes, you’ll see something like this:

Those items with the gray dotted circle didn’t actually sync—iTunes told the iOS device the files were coming (so they show up in the list), but the file itself didn’t transfer. What seems to happen is that iTunes will sync up until it hits a duplicate of a purchased song, then it just stops (without telling you it stopped).

The fix

To fix the problem, you have to get rid of the duplicates—note that it’s only duplicates of purchased songs that cause the problem. In theory, this should be as simple as selecting your Music library, then using View > Show Duplicates. I did that first, and went through the list of matches to find actual duplicates of purchased songs.

I found a few, and removed them, but sync still wouldn’t work. Eventually, iTunes wasn’t reporting any duplicates, so I was somewhat stuck. I’d then send my sync log files back to Apple (they had me install a logging profile), and they’d be able to identify the next song that caused the problem. I’d remove that one, and then we’d then repeat this process, one painfully slow song file at a time. Ugh.

Why didn’t iTunes see these duplicates? Because they’re just different enough to not meet iTunes’ criteria, it seems. For example, here’s a duplicate that Apple identified which passed iTunes’ filters:

As you can see, the artist and time are identical, but the title and album are not. Listening to each track, though, they sounded identical to my ear. When you look at the Get Info window for these songs, you can see some other differences (click to zoom, wide window required!):

Notice that the file sizes are slightly different, and that one item has a purchase date while the other does not. These differences are enough that iTunes doesn’t think these files are duplicates, but are close enough to trigger the nasty bug.

The tool

So how do you find these devious semi-duplicates, if iTunes won’t identify them? I turned to Dupin ($15), Doug Adams’ excellent duplicate finder. I tried various combinations of Criteria settings to make sure I was getting all the dupes; this one was particularly effective:

By searching on identical album, artist and track numbers, I could find all those duplicates that had different song titles (the first three songs above, for instance, all have illegitimate dupes). Not everything found would be a true “bad” duplicate, as some CDs are just weird. You can even see that in the screenshot—Counting Crows’ Holiday in Spain and Paved Paradise are both track number 13 on Hard Candy.

Instead of using Dupin to remove the dupes (which it can do), I just switched back to iTunes and decided which one to keep and which one to delete.

After I completed this process—I found about 20 such files, all much older purchases—I was able to sync my iPhone and get 100% of my content transferred—hooray!

A very important heads up

When you first connect your iOS device after clearing your duplicates, you may see this dialog:

If you see this dialog, it’s really important that you click the Don’t Transfer button! If you do transfer the purchases back, you’ll be recreating your duplicates. And that would not be a good thing to do. (Ideally, you’ll have transferred any other legit purchases prior to clearing out duplicates, otherwise you’ll need to redownload them.)

So how’d it happen?

Just where did the duplicates come from? That’s a great question, and one I can’t completely answer. Every duplicate I found was a very old iTunes purchase—most from 2003, none newer than 2009. I don’t use iTunes Match, so it couldn’t have been some automatic thing that just happened. And all the duplicates have notable changes—some have a higher bit rate, some are DRM free vs. protected, some are longer in duration, etc.

It appears to me that, somehow at some point in time, I must have told iTunes to upgrade my collection (perhaps related to the removal of DRM, many years ago?). Those new versions should have replaced the old versions, but for whatever reason, they did not.

Years pass, and there’s no problem, because this bug is apparently a recent arrival. But once the “bugged” version of iTunes was on my Mac, the duplicate songs became sync killers.

Wrapping it all up

This was a long painful process—it’s only been four days since I picked up my iPhone, but solving the sync issue is about all I’ve been doing since then. I thank Apple for the prompt response to my issue, and for working with me to get everything working again. Everyone was incredibly professional and seemed genuinely interested in solving the problem—even on a Sunday morning.

Apple’s “normal” tech support folks were also very good, even if they didn’t seem to have the knowledge to solve the problem. They spent quite a bit of time with me, making sure they understood the problem. They checked in with me yesterday, to let me know they were still working on it.

Regardless of who solved it, I’m just very happy it’s solved…and hopefully this article will help someone else out of the same situation.

242 Comments

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  1. the duplicate path paid off eventually…had an artist with a different spelling for two of their albums, when i untucked the one i already had on my phone (i wasn’t getting the ‘free download one’ on my phone), it opened the floodgate also for all my bootleg zipped songs i also couldn’t get on my phone. apple is clumsy and I’m ok with that –

  2. i think the duplicate path paid off eventually…had an artist with a different spelling for two of their albums, when i figured out the one i already had on my phone and unticked it, in the ‘sync music’ then ‘artist section’ (i wasn’t getting the ‘free downloaded one’ on my phone with the different spelling), coincidently it opened the floodgate also for all my bootleg zipped songs i couldn’t get on my phone that i downloaded off the internet to my mac. apple is clumsy and I’m ok with that, and its late now and i want to go to there bed now –

  3. Thank you so much – four months, several iPhone and iPad updates and resets, no help from the Genius bar and numerous google searches – and iTunes is now allowing me to put songs on my iPhone. Though, the duplicated songs that were causing drama for me were ones I had ripped from CDs rather than bought from the iTunes store.

    1. Same for me, well, in a way. It doesn’t appear that my problem has to do with duplicate tracks, at least not that I can tell…yet. I’ve had issues syncing ever since I went to re-encode a bulk of my 40Gbish library to 192kbps so they’d all fit on my “64Gb” iPhone 5, and what were the albums that were causing the problems? You guessed it, hardcopies. I found my way to this forum to deal with a similar issue in my iPhone seemingly deleting tracks when I sync, clearing more and more songs off of my phone with each attempt. Happened first in the aforementioned situation I just described around Christmas when I went to sync the new CD’s I received and now once again, it’s happening one I imported and attempted to sync the album that came in the mail today. I made a few purchases in the iTunes store between these two sync occasions (I believe I bought one 7-track EP and 4 singles, all totaling to 12 purchased tracks), so I can’t decide whether these or the CD tracks are the files that were the catalyst to this ongoing frustration. Like always, I’m late to the game when it comes to updating operating systems so I finally updated to the latest version of iOS 8 (from iOS 7.0.2 iirc) and now tracks are finally syncing, at least 6404 out of a library that has 6708 are, I’m kind of assuming (and hoping) that the “missing” 304 songs were already on the phone and were the remaining bunch that didn’t get wiped out from any of the 5+ sync attempts I ran tonight before trying the update on for size, but who knows. At any rate, I’m nervous as all hell to import and sync the next album I purchase (yes kids, there ARE in fact people in this world who still buy their music legally, and all CD hard copies to boot) to my phone, because the track record recently hasn’t been very promising. Or maybe it’s just something embedded in Arch Enemy records that’s sending my phone and my library to hell. Damn Swedes and their fantastic brand of melodic death metal, here I am going on an artist binge and getting potentially punished for it heh.

    1. I don’t think that’s a problem, because that’s not a real duplicate — I have quite a few duplicate song titles across albums, even with identical durations (i.e. when an original song appears on a greatest hits collection) and they work fine. It was only when the title, album, and track number overlapped that I had issues (though sometimes the title varied as well).

      -rob.

  4. thank you for finally getting to the bottom of this issue, for the better part of last year and 3 escalations to engineering I have fought my itunes library. first syncing my new ipod then my new iphone and then itunes match.

    I suspected something like this but could never get apple or myself to pinpoint the exact issue, along the way things would clear up and everyone would move on.

    so thanks for the final piece of the puzzle, as I know I have a significant number of dupes still (I cleared a bunch of them previously thinking this might be part of the problem) but now I will get down and dirty with them!!!

    congratulations to you getting farther than myself with support and engineering as well, they were great and reaaly tried to help but once I got to an acceptable functionality they were on to the next poor soul.

    Honestly I could not expect any more of them as they went above and beyond what any other corporate tech support would do “Thank You Apple Support!” but a real fix of itunes is what we all really need :D maybe Jimmy Iovine will get them on the stick!

  5. A comment about the duplicate issue I deleted all my duplicates that is not the issue. I still have the unknown sync error and my songs skipping to next song that will play. I am having to sync my phone little by little and weed out songs that do not play. I have tried everything except restoring and from what I read that will not work

  6. This cannot be serious! I have loads of duplicates – they’re intentional! Most of them are different versions of the same song by the same artist, sometimes on the same album. Who in their right mind would code a restriction on duplicate names? There are songs with the same name that are completely different; there are remixes of songs that have the same title; there are acoustic versions, remastered versions, “naked” versions, radio versions, explicit versions, clean versions. Why do I have to delete a large part of my library so that that Apple’s substandard, poory designed, coded and tested software, can cope with my library?

    …I’m speechless!

    1. Those aren’t duplicates — those are different versions of the same song. Duplicates as I discuss them are true duplicates, and they only happened with very old purchased songs. For instance, I bought track XYZ by ABC seven years ago or whatever. Let’s say it was 3:23 in length. Then, at some point, iTunes updated the track, and it became 3:25 in length. But it was still song 12 of 22 (or whatever). Both were in my library, and that’s what caused the problem.

      So your “different versions of the same song on the same album” won’t cause problems.

      -rob.

      1. Duplicate tracks is not the problem I deleted all my duplicates and I am still having the unknown sync error and I still have songs at random skipping to the next song. Apple needs to put out a update to fix. Most importantly they need to admit there is a bug

        1. Lynda:

          Duplicates is definitely not *the* problem, but it is most certainly *one of* the problems. As noted in my follow-up post, there is also a problem with extremely slow sync … and there are probably other issues. But having these true duplicates is definitely an issue.

          -rob.

    2. +1 this sooo stupid what were they thinking at Apple!!!!
      I have been fighting with synching my music from my PC to my iPad’s for over a year now and its driving me crazy….and I to am comnming to the conclusion it is more than just a duplicate issue.

  7. After reading this, just went through all 13 thousand+ songs on my iPhone, deleting duplicates. I am totally sure I got them all. Not. Not my favorite way to spend what little vacation time I have left. :b Of course, iTunes thinks it is syncing still, but it doesn’t seem like my iPhone does. So maybe it timed out as I deleted songs.

    So now I can shut down iTunes and try to resync, but risk having iTunes “forget” my changes. Or just wait overnight and hope it magically finishes whatever the heck it is doing. Or just start over tomorrow by changing strategies entirely, wiping out all music and just adding it back one album at a time on an ad hoc basis. Just unbelievable that something so simple as copying files onto a device has been turned into such a soul burning nightmare for people with large music libraries.

    I can’t tell you many hours of my life iTunes has wasted on this issue and whatever evil siblings it has still lurking. I use my iPhone heavily as a music player while in the car and exercising, and it’s been at least three generations of iPhones where my phone gets into a state where I can no longer reliably get new music onto it from iTunes, and iTunes just slips into this mystery 30+ minute silent state where it says “preparing to update” and may or may not come back. I try deleting songs, saving/restoring from backup, etc.

    I hope you grabbed Tim by both ears and didn’t let go until he promised to eradicate this thing from the face of the earth — it has caused much human suffering… :b

    1. Thank God there is some one out there who had suffered& experienced exactly the same crash from itunes.
      I am not going mad.
      I only have 4,000 songs buggy am convinced out i is an itunes portion gem,
      After about 15 hours on the phone to apple technicians several restores, having tried every solution possible I have given up.
      I will wait for an itunes fix.
      But my god what a joke.
      How long will we wet
      Wait???
      I might add
      Are….
      Ask lap a complaint
      Complaint to apple that was NEVER RESPONDED TO !!!
      NIGHTMARE.

    2. I’m tentatively ready to state that iTunes 12.1.0.71 on Win64 with iOS 8.1.3 on my iPhone 6 Plus solves the problem. Copying songs to my phone works again and goes quickly. Time will tell, but, to their credit, it looks like Apple finally got religion on this issue. Thanks to people for making Apple aware!

  8. I’ve been struggling with this as well, and nothing has helped. Until today. At least I THINK it is fixed. After connecting my iPhone 6 to my computer, in iTunes (on the computer):

    1) I selected my iPhone –> selected Music under the iPhone –>then I UNchecked Sync Music.
    A dialogue box appeared with a warning that ALL my music would be removed from my iPhone if I unchecked that box. I nervously said “ok.” When I looked on my iPhone, however, everything seemed to still be there.

    2) I ejected the iPhone from iTunes and restarted iTunes and reconnected my iPhone.
    The “Sync Music” box was again checked! So I unchecked it again and hit “Apply changes”

    3) After that, I again checked the “Sync Music” and the “Entire music library” box.
    Finally, for the first time in a week of trying many other things, a few of my newly created playlists (created on my mac) are now on my iPhone. The playlists on my computer iTunes now match my list of playlists on my iPhone!

    Note: I’m no expert and I accidentally found what seemed to work for me. No guarantees that it will work for others, but I thought I’d throw this out there if anyone is as frustrated as I have been!

    1. Thank you, Thank you, Thank you. I have tried many fixes I found on line.
      I have been having trouble for months synching from iTunes to my iPod. Ever since the last update to the iPod. Apple support couldn’t even help me. I am constantly changing my iTunes content and never had trouble synching before. The last few times I had to restore to factory settings and lost progress for some games I play that do not keep info on line.

    2. Thanks Linda!! After dealing with this problem for months, your simple solution FINALLY brought all my music to my phone. Thanks so much! No more listening to half albums for me!!

  9. Same problems with me, I got two iPods, one for my wife and one for me, hers is fine, but mine does not complete sync, misses songs, artwork…the new iTunes on my mac look great but transferring them into portable devices is unpredictable, I hope they can fix this soon

  10. And yet again, after several successful weeks of sync, it all grinds to a halt; my dynamic playlists aren’t updating on the iPhone and sync is stuck for several hours with no apparent data being copied or removed.

    The issue always seems to return when I either add iTunes store content via a playlist in iTunes or by downloading it directly on the phone.

  11. after checking for duplicates, itunes found many “duplicates”. if you have live and studio versions it calls them duplicates so i didn’t want to touch them, i have very carefully over the years corrected the mp3 tags so i know all info is correct. my syncs were not correct with music, audiobooks, movies, and podcasts. i did the network setting reset and everything was syncing. this is not the first time i have had sync problems but it is the first time on my 128gb iphone, removing and resyncing 7000 songs isn’t a quick process. a network reset is a very quick fix if it works for you.

    1. a small update, today sync stuck again, reset network settings and nothing, shutdown and restarted phone and it synced the missing podcasts and iphone artwork(?), the artwork was already there

  12. I’m having a sync issue at the moment with some of my movies. Just dumped a series (mp4 format) into my library and manual tried dragging a number of them into my phone. Some worked, while one did not (I need that particular one to watch in sequence- argh). Tried everything last night but still same outcome- went thru the “steps”, says it was syncing and nothing. Ready to pull my hair out. I do know that I have episode 13 in my library twice and that is the one not syncing so I’m glad I found your site. I’ll give it a try later tonight. Thx.

  13. Thank you. This helped me also. In my case I had a few songs duplicated in AAC and MPEG from many years ago when I wanted to compare the quality and decide how to rip all my CDs when I got my first ever iPod.

    This is a major bug, and it’s only with iOS8 because my older iPods all sync fine with the very same iTunes library.

    I’ve also noticed that the iOS 8 gets full of junk in the “Other” category of storage if you change e.g. the name or properties of videos. It’s like it copies the video again with the new name, but leaves the old one on the iPod with no reference to it.

  14. One interesting new issue I’ve noticed is that iTunes occasionally duplicates playlists in iTunes that are synced on the phone. For example, I’ll have a playlist (either standard or smart) titled “iPhone Playlist” in iTunes, and I’ll have this playlist set to sync with my phone. It will sync perfectly fine several times, but then I’ll suddenly have issues with artwork disappearing on the phone or with a smart playlist not updating on the phone. It’s then that I’ll notice that I now have a new standard playlist in iTunes with the name “iPhone Playlist 1” with the exact same content as what is on the phone, however BOTH the original and the new playlist are checked in iTunes to sync. I wonder if this has something to do with the updates or artwork not carrying over to the phone?

    Why am I troubleshooting Apple’s device for them?

  15. In four days’ worth of work, it’s almost right. Thanks for giving us details to work it out!

    As an unpaid youth minister I rely heavily on samplers and then purchase what I can use later, so I have (now had) lots of duplicates which really weren’t. I converted all my MP3 s to AAC. Then deleted or stored the old MP3 s in a distant folder. Then checked again and still had songs (I’m going to have many versions of Silent Night after all) that had to be sent into hiding in a different folder. Just unchecking the boxes didn’t help, so moving and/or deleting after converting was best for me.

    Had to restart the Mac a few times.
    And my iPad has that ‘also wonderful glitch’ in the hardware that shuts down the sound until you perform a hard reset. Had to that three times before and after syncing. Now my music is mostly working. It duplicated a music video without permission and lost some of the album covers and scrambled a few, too. I had to give up on a few titles where the covers or the sorting was out of whack, but it works overall just in time to take my iPad to work.

    Now why is it when I start iTunes on my iPad it can’t remember where I was when I used it last? I never want to start at Radio! I need it to remain where I was because I won’t always remember it myself and we are in a hurry to start on time.

    Don’t know what to do with ancient protected purchased files linked to an old email address and ID.

    As for the playlists, they have some strange sorting going on, but at least my music is now available. This is so Mac unlike.

    Mac user since 1985 and growing increasingly frustrated!

  16. Thanks so much for this article!

    I’d recommend a slight change, emphasizing to attempt the “show duplicates” step first before proceeding, because that fixed my problem and I didn’t have to do further digging.

    Regardless, thanks for the article!

  17. I had no duplicates, so I chose to go into my iPhone’s settings (with the phone unplugged just to be safe) > General > Usage > Manage > Music > Edit > remove “All Music”.

    Once my phone deleted all of the music from its memory, I was able to plug it back into my computer and sync the correct music I wanted to with iTunes. This isn’t the first time it’s happened. I think at some point, music becomes corrupt in the iPhone, and it messes with all other music syncs from that point.

    I find randomly deleted songs all the time, randomly ADDED songs that I NEVER chose to have added to my iPhone… It’s REALLY glitchy. I hope Apple gets on their sh*t and fixes this – it’s ridiculous. The way iTunes downloads purchases to every device is messed up too. Some purchases will show, others won’t.

  18. The Iphone update 8.1.3 that they just released fixed this problem for me. It’s been so annoying not having all of my songs on my phone. Thankfully now all of my songs are back where they should be :-)

  19. The 8.1.3 / OS X 10.10.2 update alone did not solve this for me. I finally decided to use iTunes ‘Restore’ function, and only sync my ***** (5 star) music to save time if the Restore did not work.

    It DID work! Wow!

    So, I then clicked/turned on other Playlists that I wanted synched. No Joy….

    Did another ‘restore’ (4 Star and 3 Star Playlists still enabled), and let it sync overnight.

    Hello music!

    (Sigh)

  20. Not one update of iTunes has worked for me. My duplicates are diverse and most are not “duplicates”. For example, I have about 100 audiobooks that I ripped to iTunes prior to using Audible. Those books are all in my duplicates list, even though every chapter is named differently. Seriously? In order to sync the rest of my music, I have to delete all of these books? That is not a fix for me. Furthermore, every audible book that I’ve downloaded no longer syncs. I just get the greyed out circle. Completely ridiculous.

    1. Those aren’t duplicates that will cause the problem I’m describing here—these were true duplicates, almost all of really old iTunes purchases that had been updated at some point in time.

      -rob.

  21. Thanks this seems to have fixed my problem of a 1.5gb ghost movie. Turns out because iTunes was getting stuck, it could never finish processing the removal of that movie. I selected all purchased songs, receded them with Max and added them back to iTunes. I didn’t need to delete any duplicates.

      1. I’ve got the same bug and de-duping is not going to happen. I’ve got a collection with a lot of versions of live music. Same song title and artist sometimes different lengths. This bug is killing me.

        1. That’s not the cause of this problem—it only relates to songs purchased from the iTunes Store, that iTunes updated at some point in time. In my case, there were new durations, different album titles (slightly), etc. But 100% of the tracks were iTunes store purchases.

          I still have tons of “duplicates” in my collection, but they’re like yours … if you’re having sync issues and you don’t have any of these “purchased duplicates,” then it’s something else that’s causing the problem (and I feel your pain).

          -rob.

  22. FWIW I found that my problem with syncing was self inflicted. I want cover images on songs so if I buy a CD and copy it to iTunes I will always get the cover image image. if it doesn’t get it from Gracenotes then I scan the cover and import it to the album or song track. what i found was that on this occasion I scanned the cover image with the resulting jpeg being over 6megabytes. This was way too much for iTunes to sync to my iPhone 4S and once I removed the last cover image I scanned everything went back to normal syncing. This has been over 3 weeks now and no glitches. Hopefully my solution might trigger something with causes for why you may not be able to sync correctly with your devices.

  23. I’ve had problems with tracks from old burnt CDs and also brand new purchases from Amazon MP3 downloads that auto sync to iTunes (unstoppable) and the won’t sync to the iPhone (unstoppable) . Cmon Apple – this is crap. Time to sack someone on the iTunes team.

  24. I upgraded to IOS 8.2 yesterday and was finally able to sync without deleting the >1000 “duplicates” (NONE of these were actual duplicates and I did not want to risk losing all that music by deleting them, so I’d been unable to sync because of this). So that was a happy event for me. My only remaining issue is I still cannot play Audible audiobooks even though they synced to my iPhone 6. I play them from the Audible app, so I’m not completely stuck, but the functionality in the music app is better to advance or reverse tracks than in the Audible app.

    1. Perhaps because we don’t want to spend $60 on an app that replaces something we already paid for, and that should work? Perhaps because we don’t trust a company that relies on MacKeeper pop-up ads on their web site? Perhaps because we prefer not to involve a third party app in the core sync function?

      For any number of reasons, that’s why. Note that I have edited your comment to remove the insulting language; please keep it civil.

      -rob.

  25. iOS 8.2, iTunes 12.1.0.50: The problem is still there. I purchased one song in iTunes and then purchased the CD in a store. After ripping the CD and importing into iTunes (with a duplicate warning), syncing to iTunes failed silently. No more new songs could be copied. Deleting the duplicate (purchased/ripped) did solve the problem.

  26. not paying for a tool to fix apple’s bug… i switched to streaming media, rdio & sporify all together and stopped buying stuff from itunes, easiest and quickest fix

  27. Still struggling with this bug late at night. Will try again tomorrow, come on Apple, this ain’t good enough!

  28. aaarrrhhhhhggghghghg. This bug just won’t go away. Running iOS 8.2 and iTunes 12.1.0.50. I was OK for a couple of weeks and now it is back. What the heck is going on, Apple??? How can we get their ear again to fix this problem???

  29. I deleted some files that I thought were duplicates, and then the sync worked! Today it’s broken again!!!

  30. Hi all, i have had the same issue for a few months and massively annoying beyond belief. i like most others had tried all fixes i could find online – but tonight i deleted iTunes on my Macbook pro running 10.6.8 and reinstalled an older version of iTunes from Apple’s site – and bingo! full syncing with music and my apps! then turned off the auto update (i did try to run new version of iTunes available but it will not run on my now old machine) I am surprised i did not see this solution any where.. hope it is helpful for people struggling out there – why the hell have apple not solved this issue is unbelievable TBH.

  31. Apple’s quality control is just ludicrously bad these days. I am having gray circles again. There is no way to figure out the cause. I don’t have duplicates. It’s maddening. I wish there were an alternative, but we are forced to used this ludicrously bad program to load the files. iTunes 12 is a horrendous step backwards and is far far worse than 11 or 10. I would revert if I could. PLEASE FIX THIS MESS, APPLE.

  32. I only have access to my laptop once every six or so months; after updating iTunes to 12.1.1.4 and updating my iPad to ISO 8.2 the syncing deleted 2000+ songs on my iPad. After scouring the internet for four hours I have tried the duplicate method and it worked! iTunes is currently copying the songs back onto the iPad. My songs were duplicates I had from different sources (ie. my CD and a friend’s CD). Thank god I only have around 3000 songs to scroll through. I would much rather spend the time painfully hand picking then on the phone with unknowing support staff. THANK YOU THANK YOU THANK YOU!!!!

  33. I used this, in conjunction with iTunes dup finder. Still had some weird low bit rate purchases showing up, but these are not preventing me from transferring files to iOS anymore. Thanks.

  34. I was having this problem, and just solved it with minimal hackery. It seems like Gracenote could use some data scrubbing.

    1. After deleting or hiding dupes, etc., go to the album that will not import to your iOS device in iTunes.
    2. Select all the tracks from the album (shift-click the first and last tracks)
    3. hit command-I for a “get info.”
    4. Click yes, that you want to edit all items. Look at the artist, composer, album artist, etc.
    5. I just copied-and-pasted the artist name into the “album artist” and “composer” fields, which were blank. Also, in one case, I un-ticked that an album was from various artists. (Which it was not, and which I’d not set before.)

    They then came over on subsequent syncs. Your mileage may vary, but this worked for me.

  35. I have had this problem for a long time. I also don’t know when it popped up. I have transferred songs between libraries, synched many devices (several iphones, ipods and ipads) and the like so the duplicates probably snuck in that way. Until I found your article, after looking periodically over several months, I finally understood what the dotted circles were and how to fix it. It only took about 25 minutes armed with the find duplicates and deleted them as you show above to get the library on my desktop and my iPhone 6 plus fixed. Thank you!!!!!!!!!!!!!!!
    Now on to the other devices…

    1. I don’t have any direct recommendations, but I found this article, which includes links to a couple of third-party apps that might help.

      regards;
      -rob.

  36. I need some help need somebody take on this I have iOS 8.4 on iPhone 5s iTunes 12.2.1 and I am getting the iPhone sync error again every time the tracks that are showing up in duplicates are not duplicates of anything in my library What is the problem I am open to feedback. Thank you
    So much

    1. You may have to visit an Apple Genius to figure out the exact cause. If you want to try to troubleshoot, start in the Console application and look for iTunes-related issues to see if there are any pointers there. But it’s a dark confusing road, figuring this stuff out, and I can’t really provide any useful support on a one-to-one basis.

      regards;
      -rob.

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