The Robservatory

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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.


  1. Wow, this could explain why I've been having so many syncing problems too (although my iPhone 6 has been hanging simply trying to install apps, even before it syncs music). Genius Bar appointment booked today so hopefully they're aware of all this...

  2. We're seeing this problem unfortunately, and we don't have any purchased music. The silent death thing is just another example of how far Apple has fallen - burned hours trying to make the "it just works" misery do even a basic job. Hoping the fix comes soon; if mum's new phone wasn't a donation she'd be sending it back for an Android right now.

  3. Thank you very much for taking the time to contact Apple and, mostly, reporting everything like you did. This thing was driving me mad, returning my brand new iPhone even crossed my mind.

  4. I don't have duplicates in my purchased folder and they are not showing up as you stated earlier for me. However, I still cannot get my music to sync properly and after paying quite a bit of money for the 128 GB, I think I don't want to pay for something that apple should fix for free. I'm getting fed up with this.

  5. If this solves my issue, I will stop contemplating finding an alternative music player (I was even thinking of bringing my iPod 10 GB out of retirement). Not syncing music is a real deal-breaker...

  6. Thanks for posting this -- I've been beating my head against my monitor trying to figure it out! :) Hopefully iTunes 12 comes out next week and fixes all of this!

  7. Wow I can't believe I've put up with this syncing issue for almost a month. Thanks for posting this, deleting duplicates resolved things for me.

  8. I have found another iTunes issue since the iOS 8.0.2 update. Causing some of my songs to be labeled a song of the first artist I open after restarting.

  9. Been dealing with this issue since updating to iOS 8.0.2 on my iPad 2 and iPhone 5... I have tried duplicates and all sorts of things... rebuilt library from scratch (admittedly helped me clean out some other errors like certain songs not playing across the network on airplay)... but for some reason tonight after i turned on 'in the cloud purchases' under the store preferences... my iPad and iPhone both started syncing without me telling them too... and presto... it synced my music files to both devices completely... all i can say is Apple... WTF...

  10. Thanks for writing up this fix. You can't get a sorted playlist to sync without disabling Live Updating by adding Playlist is Music as a criteria, and even then iOS 8 has broken that. Live Updating never really worked right all the time anyway. iOS 8 also seems to have broken Automatic Downloads. How can Apple claim to be "all about the music"? Just because you trot out U2 at your keynote doesn't make it so. Very disappointed with iPhone 6/iOS 8. Thanks again for your efforts.

  11. Hi Rob, just read your article. Had kind of the same problem with syncing. My setup is a MacBook Pro Mavericks 10.9.5 iTunes 11.4 and iPhone 4s 64Gb with IOS 8.02. Everything worked good with IOS 7 but made the mistake(?) to upgrade to 8.02. I did a sync with itunes. Result was a large yellow bar with only 'other'. All the music +50Gb was gone... Again syncing seems to work, Audio was showing. After an hour or so with the last songs being 'synced': gone was the audio again! Did reset on iPhone and tried again, same result. Restored iPhone, different result but only half the songs got synced. Searching the net I read something from somebody writing about your duplicates article. Did not read the whole post but looked in iTunes library and found about 30 duplicates, but not one exact duplicate all on different album, live versions and so. I changed the song names with an added 1, 2, 3 etc. as version number. Did a sync and: everything worked! Checking my library after reading your article I found only 2 duplicates in purchased and 'normal' songs but again no exact duplicate, cannot see that as the reason for the strange behavior. What I did see was (for instance) in my Beatles collection that nearly all the songs from the 'Love'-album where omitted from syncing with the original albums or the other way around. These where of course NO exact duplicates. Pretty sure there is a bug in the music app database in IOS 8.02. Anyway, changing the song names with version number did the trick for me...! Hope some people will be helped with this post. Waiting for iTines 11.5 or IOS 8.03. Thanks, Gerard, Amsterdam, The Netherlands.

  12. Thhanks much for this bug report on the duplicates in IOS 8.0. I cannot seem to solve my problem with playlists after deleting all the duplicates. Did Apple say they are going to fix this? and When?

    1. They did say it was fixed, and would be out "soon." I'm guessing it's either in 8.1 or iTunes 12, both of which could be out as soon as today.


      1. I am so disappointed that neither update resolved the syncing problem for me.

  13. Thx Rob, you have been the most helpful with this issue. This is not imperative. You think I should wait for the updates to iTunes and IOS?

  14. Rob, just downloaded the new iTunes (12.01) and IOS 8.02. Still no luck seeing my playlists on my iPhone. Hope it is just me doing something wrong

    1. #mcdonaldmorgan: You have to sync the playlists from itunes as well... I have them all and it works flawless. Non on itunes 12 yet...

  15. Gerard, No can do...been trying all the tips from all, and still cannot sync any of my iTunes (12.01) playlists to my iPhone 5s (8.02).

    Very disappointing and annoying that this is happening to me and many, many more.

  16. Can anyone help, please! I can no longer see any songs on my iPhone 5s (8.02) and can no longer sync from iTunes (12.0). Cuz I am sooo ticked off, Apple no longer allows me to post to their "Discussion" lists. Not good. Any Help would be appreciated.

    1. Did you do a restore? If not try it, but make a backup first... See my previous posting...

  17. I discovered that duplicates were the source of this problem for me about a week ago. I'd like to throw in a couple of wrinkles:
    1. The lengths of the songs do not have to be the same; in my case the two songs were entirely different durations BUT were listed as being from the same album.
    2. In my case, one of the songs was mislabeled and was apparently put on my computer by iTunes Match. It was labeled as a duplicate of one of my songs, but in truth was a different song from the same album.

  18. With whom can we address this issue? I have no more patience. it is shocking that the iTunes update nor the iOS 8.1 update has resolved a syncing problem with our music!

    1. You can try what I did, and write a reasonable-tone email to Tim Cook, explaining the nature of the issue. I honestly don't think I got a reply because I was a "somebody," but rather because the problem I was having was something they wanted to solve.

      I would also advise calling the support line, as they're usually very good -- the staff that I spoke with was working hard to solve my issue, and probably would eventually have found the answer.


      1. I have to say..not true. I'm sure they want to help but I generally have to go through 2 of the phone support staff to ever get the right answer. And on Sat, 11/8 when I called re this same exact synching issue I got 45 min of hemming and hawing and was transferred 3 times. The duplicate issue never came up. If it's a known quantity, of at least a month, then it should have come up immediately.

  19. I managed to fix my syncing problem by doing 2 things. I looked for duplicates and deleted only a few files out of ~4500, but I also noticed that there were a few files that wouldn't sync because they were in the wrong format (in my case video files, but it probably could be anything). To see if you have this problem do the following: Connect your phone to iTunes, look at the Summary tab, at the bottom in the Options section, click the Reset Warnings button, then sync. Clicking that button means on your next sync you will be warned of any photos, videos, apps, etc. that can't be synced. After ensuring those wouldn't get synced to the phone anymore, I then looked at all the songs on my phone for the gray circle. That indicates a song that didn't sync properly, and on my phone when I would try to play one of those songs it would just skip to the next song and play. Those songs would never play, probably because the file isn't completely there or it's corrupted. To find those, in iTunes click the arrow next to your phone in Devices to expand the contents of the phone. Click on music and scroll through the whole list, looking for a gray circle at the far left. I unchecked those songs so they wouldn't get copied (I have "Sync only checked songs and videos" checked) then synced. Now it synced without any warnings, and I rechecked the songs I had unchecked, synced again and everything was good. I don't know if it was just unchecking and rechecking the "bad" song files, or eliminating the videos with the wrong format or both. I did read somewhere that a corrupted file that can't be synced can cause the sync to fail at that point instead of gracefully skipping the bad file and moving on. And I believe that is a new problem to either iTunes 11.4 or iOS 8. Good luck!

  20. i had the same problem prior to update to 8.1 on my iPhone 6 (i did today) which solved the issue. i don't see any greyed out music on the device in iTunes and all the music seems to be there now on iPhone.

  21. I am still having the exact issue described despite updating to iTunes 12 and iOS 8.1. If I go through removing the duplicates, should I do an erase and restore of the iPhone 6 Plus before trying to resync?

    1. I didn't have to do that; after removing all the dupes, sync "just worked."


  22. Using iTunes 12.01 iOS 8.1 and OSX 10.9.5 MBP and iPhone 4s 64Gb. Unreliable, sync does not work OK. Have about 12.000 songs, > 56Gb. Tried that wirth full factory restored 4S. Sync whole library got stuck on 'waiting for changes(...)' waited overnight, still stuck. Was able to sync everything manually with separate syncs for all genres, took about 4 hours. Forgot to mark sync only marked. Tried that and got stuck again, iOS 8.1 deleted about 80% of all songs previously synced, it seems to go on with syncing after ejecting iPhone: the sync circle kept on going round. Tried to start fresh again, but unable to delete music via iTunes, unable to delete music via settings: Setting app hangs. Was able to delete all music again separate by genre via iPhone music app, after that finally empty music on iPhone. New try syncing all genres separate with only checked songs manually worked, again 4 hours... Have now what I wanted, about 9500 songs on my iPhone. Will not sync again till new iOS update... Apple please give us back the latest iOS 7, as there where never ANY problems. Specially for 4S users, as I believe iOS 8 is not OK on 4S. Note: on my old iPod Classic 160Gb everything works flawless... Cannot believe that music, the first thing Apple did with iPods is not working OK with my 2 years old 4S and does with iPod...

  23. Wow. What a pain. Maybe I should have just skipped the 64GB version. Good thing Spotify works across all my devices. Honestly, this is why I hedge my bets against lock-in to any one provider.
    This has been working with no issues for how many years?

    1. For as long as I had iPods never any issues, I had the first iPod somewhere in 2001. Never any issues with iPhones till my 4s update to iOS 8...

  24. I was thinking about having the new ipad and/or Iphone 6. But those repeated bugs in minutes, safari and others make me reconsider the question. I don't want to spend my time trying to resolve problems because Apple is unable to test its softwares before selling them!

    1. Sorry Christian, Akruto is a Windows only program and syncs with Outlook, and does no music...

  25. I had issues with Purchased songs too. But they were not duplicates.

    When I first set up my new iPhone I had 80% of the album art missing. It drove me mad and after a few hours of trial and error I just erased the iPhone and re-synced plyalists one by one. The album art went back.
    Then I upgraded to iTunes 12 and iOS 8.1. After the 8.1 update, I lost all the album art of my songs, and all my playlists. The playlists had just disappeared from the phone (I have 20 or so). Also, I had the issue you describe where songs did not sync to the phone and appeared grey in the "on my device" section. When I would try to play one of those unsynced songs on the phone, it would skip to the next, to the next, to the next, until it hit one of the few songs that was actually stored on the device.
    I tried the same thing that worked last time, deleting all the songs and syncing again. Playlists and album art went back ... except for my purchased songs. I tried for a few (more) hours all kinds of resets on the songs, changing album art, clearing and redownloading, deleting and re-importing... in the end what worked for me is to clear and redownload all my purchased songs. They came back with the album art and synced. What I think those songs had in common is that they were all purchased, and all were edited from the iTunes Store values (title, album name, genre)... the purchased songs that were not edited seemed ok, their artwork is there.

    Anyway, I will never get those hours back and I am pretty disappointed in Apple for letting iTunes degrade to a Microsoft grade software "quality". A simple Mac to iPod USB sync used to work fine from 2001 to 2011 or so (when they started adding iCloud and iTunes Match to the mix). It's been downhill from there.

  26. I have been grappling with this since I got my iPhone 6, and this solution does not work for me. (I'm running an iPhone 6, 10.9.5 and iTunes I did have a couple duplicate purchased songs that I deleted. I also have many non-purchased songs in my library that have duplicate titles as I listen to many bands that allow their concerts to be taped. They are not actually duplicates in the sense of being the same file.

    As I posted here ( the only reliable solution I have found, which is actually simper than what I posted on the Apple support site, is to:

    1. Sync iPhone

    2. After sync, open the Music app on iPhone and press play. The phone will play through the library, immediately skipping any songs that are not actually on the phone.

    3. Re-sync iPhone; iTunes and iPhone start to cooperate and the music will actually transfer.

    This must be done every sync. It works reliably, but is not fun. I've essentially stopped syncing my phone, which for a person who backs up to computer (not iCloud) is a pain.

    1. Does this really works...? Apple, do you read these posts? Please mr. Cook DO something about this ridiculous bug!!!
      I do not want to sync again, do not like to do it again, playlist after playlist, another 4 hours....

  27. After weeks of effort with my iPhone 6 and four wipes, including several dozen failed sync attempts and errors that included issues like artwork being removed, tracks missing, and the iPhone filling the "other" space with un-synced songs, the only solution that has worked consistently for me was to remove ALL iTunes store purchases from my playlists and syncing only those files that I had ripped myself. I then re-downloaded the purchased tracks that I wanted directly on the iPhone.

  28. OMG.....Thank you thank you thank you thank you!!!!!! This is exactly what has been happening to me and I have been beating my head into the wall trying to figure out what is going on. I was about to completely delete my entire music library and re-add it to itunes...which would have taken ages since I have almost 2000 songs. But, I decided to do 1 more google search and I found your article and it now works! THANK YOU!!!!!!

  29. I seem to have the same problem, even under iOS 8.1. I see the dotted circle you mention under the iTunes list of songs on my phone, but how do you delete it? When I search the computer's full library of songs, there is only one version. So the duplicate is on the phone itself? How can it be deleted?

    1. You cannot delete the songs with dotted circles... These songs are NOT on your iPhone, but (I think?) only as an entry in the iPhones library, and are 'waiting' to be synchronized by iTunes, but that never happens... Try syncing again...

      1. Syncing again does not work as the sync never completes. That is the main point of the article, I think. But the author, Rob Griffiths mentions deleting the duplicate. I was asking him how exactly he did it.

        1. I just ignored them—they're not really on the phone anyway. If you fix the sync, the dotted-circle songs will be replaced by actual songs. The only way I got sync working was to remove all the duplicates from iTunes, but as seen here in the comments, that's apparently not the only cause of this problem for others.


          1. Oh, I see. But what reason is there to think that duplicates is the reason for this? How are the two things related?

          2. There was no reason to think duplicates were the cause until Apple told me that duplicates were the cause of the sync issue :).


  30. I followed your advice but I got over 80 duplicate songs according to Dupin. I do not have the time to fix this. Apple is taking way too long on this...

  31. I’m having the same problem with NEW songs. There is a new album I just bought and downloaded on iTunes in the past week. Now suddenly, almost half of them appear with gray dotted circles. ITunes detects no duplicates. I also have the problem with many other albums

  32. PS: I’m using, Using:

    MacBook Pro (13-inch, Late 2011)
    OSX Yosemite Version: 10.10 (14A389)
    Processor: 2.8 GHz Intel Core i7
    Memory: 8 GB 1333 MHz DDR3
    iTunes Version:
    iPhone 5 64 GB with iOS 8.1

    My wife has an iPhone 5S and given my troubles with iOS 8 (all versions), I’ve left hers on iOS 7.x and she hasn’t had problems.

    1. My wife's beloved 3GS 16Gb works flawless... As did my 4s with iOS 7. After the 4s upgrade to iOS 8 nothing but trouble...

    2. Hi Steve, I have also a 160Gb Classic, no problems at all, flawless syncing >60Gb in about 1.5 hours. Could be your iPod, did you try full restore and total sync?

      1. I have wondered if Apple/iTunes doesn’t like it when I change an album’s info so it sorts differently. EG, I don’t want an album sorted as “Greatest Hits of Billy Joel” and in alphabetical order is under “G”. So I change the sort field to “Billy Joel Greatest Hits” so it will sort under “B”. Maybe iTunes music database in the sky sees this purchased album as incorrect and downloads it again so it matches its database.

        I’ve bought and used Dupin to find and eliminate duplicates. It didn’t find any that I hadn’t already found through iTunes “Show Duplicate Items” function and didn’t find any of the Grey Dashed Circle duplicates.

        To try and fix it, I’ve gone through (a) Restore Backup; (b) Restore iPhone and select to Restore from Backup; (c) Restore iPhone and select Restore to Factory Settings as a “new” iPhone, not using Restore from Backup at all. In all cases, I do this manually through USB link to my MacBook Pro via iTunes (IE, no automatic syncing upon connection). I have Wifi Sync turned off so I can’t “confuse” the iPhone and I don’t have MusicMatch turned on which might confuse laptop vs. Cloud syncing and downloading.

        (a) Is of no use at all;
        (b) Usually does the trick but then takes a LONG time for my 9,843 songs to reload and all 82 Apps to reload. Then within a couple of days, the dreaded grey dashed circles or phantom duplicates appear again. These are songs of all types (old purchases, new purchases, songs from purchased CDs) — I have no pirate or grey market music — it’s all paid for.
        (c) I resorted to (c) figuring I would erase absolutely everything and start over so there was no historical baggage to cause problems. In advance, I printed out screen shots of all my 82 Apps and their group folders so I could manually set up and organize my Apps the way I want them — that takes forever — AND, Again, after a couple of days, the problem occurs again.

        So still no solution for me. I’ve also done what Greg T. suggested below on Oct 30 ’14 at 3:57 pm. My Music is all fine on the iPhone 5 at the moment… BUT, I haven’t synced again. We’ll see what happens next time I do.

        1. Hi every one
          Me again
          Would just like to add
          You are not going insane
          We all exactly the same issues with iTunes sync....
          If and it is a if I get answers after my engineer call back from Apple today I will of course share my wisdom.....

        2. I have an Iphone5 with Itunes 12 and ios 8.1 I have experienced syncing problems with the "Other" section being bloated with 7.95GB. My library is 10000+ songs, so I only put small playlists on my phone 200-300 songs. I still have problems when I want to change the playlist on the phone. Somehow many of the songs from the old playlist remain on the phone. I solved the "Other" issue by restoring to backup, but I still struggle everytime I want to sync a new playlist. I can't imagine dealing with an entire library on a 16GB iphone. Prior to itunes 11, syncing was a simple process. Not anymore.

  33. I currently am waiting for a call back from technicians at Apple.
    The problem is worth the engineers.
    Latest iTunes
    Mac book pro
    IPhone 6 plus 64gb 8.1
    Sync others bar issues

    Why isn't Apple fixing it?
    It's their issue....
    We're all waiting hours & hours
    Very poor

  34. I commented earlier in the week that this solution didn't work for me, and related what I'd done (up there ----^ ).

    After seeing more folks saying that removing duplicates worked for them, I decided to give it another go. What I discovered was that the duplicate purchased songs that I'd removed were still there. I also found a few non-purchased (that is, ripped) songs that were also duplicated. In the Finder, these had filenames like song-1.mp4 and the like. I used the View>Show Duplicate Items command in iTunes to find them.

    Where you choose to invoke Show Duplicate Items matters. Doing in it the smart "Purchased" playlist didn't work; I had to do this in the main Music library. inAfter finding them, I right-clicked and selected Show in Finder, then deleted the duplicates, choosing the "Move to Trash" option in iTunes. I then emptied the trash in the Finder.

    Lo and behold I can now sync with no issues. So there you go -- Rob, your solution works, as you'd probably already robserved. Thanks for posting.

  35. I might add that I am experiencing this syncing type of problem with my 160GB iPod Classic. iTunes 12 is taking forever to sync, I've tried to restart the sync several times but the spinning sync icon continually runs, while my iPod Classic screen face simply indicates "Connected - Eject before disconnecting", no indication of syncing. This is getting old very fast.

    1. Hi Steve, I have the same iPod 160Gb classic, no issues at all: Can sync >60Gb songs and video / photo's flawless in about 1,5 hour. Maybe its your iPod; try reset and a full sync.

  36. Just my two cents... I've spent days trying to sort out this problem. Very annoyed as I had just got a high-capacity iPhone so I could finally store my whole library on it, only to encounter this issue. My problem was that it was getting stuck on 'Waiting for changes to be applied' and wouldn't copy anything. Was upgrading from a 5, and so upgraded IOS, OSX, and all the rest of it at the same time, never had this problem before but was never trying to sync so much before, I guess.

    It synced everything when I first set up the phone (and was restoring it from a backup), but then after that it wouldn't sync at all. Tried all sorts, restoring the phone from a new backup, using PhoneView to delete random iTunes data files from the phone and rebooting it, signing out of the iTunes store, changing the sync methods and what I was syncing, signing out of iCloud. Frustratingly, I managed to get it to work once randomly but then it stopped after, for no reason I could discern. It just seemed so random, still don't know why it worked in the initial sync.

    Anyway, I didn't follow exactly what was laid out here (or use Dupin), but it pretty much solved my problem.

    I used iTunes to 'show duplicates'. Sorted by Media Type. Any which said 'Purchased AAC File' I simply did a 'Create new AAC version' within iTunes, and then deleted the Purchased ones I'd just converted. I also had a number of old 'Protected AAC Files' from back in the DRM days. Most of which I deleted, some I did the old school burn-to-CD-and-re-rip method on. Once I had cleared all the duplicates of 'Purchased' or 'Protected' files, it synced fine. I've added and removed stuff a number of times since and it's worked each time now.

    As a side note, I did this with iTunes signed off on my iPhone (but signed on on my iTunes, and I also 'hid' any purchased files in my iTunes Store Account). Passcode was switched off, and was syncing the entire library with 'only checked items', and no videos at all.

    1. Update here - This worked for a while but somewhere quite soon along the line it stopped syncing, stuck on 'Waiting for changes to be applied' again. I realise now it may be because I edited one of the 'protected' AAC files when I was fiddling around with my library. So I decided to see if it was a better idea to just not sync any protected files at all. I...

      1) Restored iPhone from backup, but didn't re-sync music.
      2) Created a new Smart Playlist featuring all songs in the library which are checked.*
      3) Made sure that in iTunes no 'Protected AAC files' (i.e. songs purchased on iTunes years ago when they still had DRM) are checked. No videos checked either.
      4) Sync just that playlist.

      * No idea if this made a difference form what I was doing before, which was syncing entire library with 'just checked songs', but anyway. And not synching any podcasts or voice memos yet either.

      So yeah, with me, I'm not sure whether it was a duplicate issue or not, the key seems to be just keeping the protected AAC files out of the sync altogether. I've synced at least 8 times now making all manner of changes from removing, adding, editing albums and all worked.

  37. Hi Rob,
    This article was an absolute godsend. I just unticked all my purchased items and sync started perfectly.
    I was just wondering when it comes to actual duplicates is it 2 purchased items that clash or as long as one is purchased. Was going to try and put my purchased tracks back on my iphone and was wondering what to avoid.

    1. I'm not sure—for me, it was just getting rid of all the duplicates, which in my case, were all purchased songs.


  38. Last night iOS 8.1.1 seeded to developers... The solution? Keep my fingers crossed...

    1. Oh I hope so. I have followed the instructions from this site and others and nothing had helped for me.

      1. It didn't help me either, Pee Jay - still won't sync properly. (Though I haven't tried the Dupin thing as it galls me to spend money on something to solve Apple's problem.)

  39. This is the 3rd new-version download I have done on iTunes in which iTunes messed up my files. Remember when they forgot to put in a delete button on the drop down menu for new, not-yet-downloaded podcasts? And you also could not hit your shift key and delete a whole row of podcasts at once? Took them over a month to fix those bugs. Now, I just downloaded the v.12 iTunes and it did not automatically sync my entire media library. It's under the iTunes file header but I can't drag and drop or somehow get it into iTunes so I can access it again. Anybody have any ideas on this one?

  40. Spent the weekend going crazy trying to fix my fouled up iTunes library. Think I got it but I bookmarked this excellent article. Now I'm trying to get my 5000+ photos onto iCloud and that ain't easy either, but I'm learning all the quirks.

    It blows my mind and infuriates me that Apple, the company that invented the coolest music players and phones, brought the music world together to create the downloadable music store, can't make a software interface that makes it all work. It is getting better but basically iTunes is a very weak link in a strong chain of hardware and software innovations. I hate it, It's crap. I've gotten screwed so many ways, so many times by iTunes and wasted hundreds of hours dealing with it over the years. Love Apple, but this is an ongoing blemish on their stellar list of achievements.

  41. This may explain some of my issues. Although since having this issue I have deleted my whole music collection off my IPhone in an attempt to fix; which is fine but for some reason the 'Other' bar has increased by approx 33Gb (the size of my music collection). Thus now leaving me little room to put any music back on the glorified paper-weight!

    Def thinking about a change next handset if these guys don't get their shit together. Havent had music on a portable device for weeks now!!

    1. Had the same thing... With me the library on the iPhone was corrupt. Check if there is any music in the music app, try delete everything by hand on the iPhone. Otherwise, sync iPhone with nothing checked in iTunes, it will 'empty' music lib.

  42. Thanks for write-up. I've been having this sync problem too. I'll give this a whirl.

  43. This is driving me crazy. I have probably a 1000 duplicates so deleting the duplicates is certainly not an option for me (especially with 3 young kids). I have an IPhone 4S and have updated software on that and my iMac. Wishing I hadn't now :( None of the answers above are going to help me. Anybody have any other bright ideas. When I click Sync, it very quickly goes through steps 1, 2 and 3 and then says completed but I think it's everything BUT the music is syncing. None of my playlists and my music that was on there has almost all disappeared - and has not put anything new on. Also saying I have lots of photos on there, when I have none (I deleted them before the sync). HELP!!!!!!!

  44. Many thanks, this has been driving me around the twist too, Dupin worked a treat - best $15 spent in a long time!

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