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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. This is crazy. Even after updating my i6 again! it still isn't working. I should be able to have duplicates so I can have a complete album. Apple needs to fix this and that's that. I have redone my phone I don't know how many times. I have deleted the phone and restored I don't know how many times. I can tell you I have spent too many hours on this every evening to only have a different amount of music on my phone each time.

  2. Just updated my 4s to 8.1.1 First report, 1 minute after restart and trying to sync: to bad, NOT fixed... iTunes hangs(?) - waiting for items to copy - and the dreaded dotter circles reappear in music 'on my device' ...
    Thanks Apple!
    Waiting for 8.1.2...

    1. I updated my 5 to 8.1.1 and I also can report that it has fixed NOTHING as regards to the hanging sync issue. I am so angry at APPLE~!

    2. My wife & i had the same problem with our I-6 ..... but i don't have any duplicate music.... hardly any music to speak of. it just WONT sync properly. NO pictures, NO reingtones, NO apps!!

  3. UPDATE: First waited for half hour. Left iTunes sync on during lunch, came back and: everything was synced... No more dotted circles... Took about one hour, (with iPod Classic 2 minutes) Also, before the sync I left purposely 'dupes' and 'old purchased protected' / 'new purchased' songs in iTunes.
    Happy to say that it is working, but give it some time... Hope it works the same fore everyone!

    1. Hi Gerard. Thanks for your message. What did you do in between the first attempt that did not work and the 30 min break?

      1. Did not do anything... iTunes stated: waiting for items to copy. Nothing was happening, I just left it in that state. After lunch came back and it was finished... (Did the same thing last week with iPod and it finished after 2 minutes)

  4. I've been following along this discussion and trying the various suggestions with limited success. Thank you all who have contributed.

    With 8.1.1 my 4s is improved (time will tell if it is actually fixed). One thing I have noticed while syncing music is that while iTunes is waiting for items to copy (and at least once after iTunes said it was finished), if I go into Music on my phone, at the bottom of the song list it will say how far along it is on downloading. It was odd the time iTunes was done, but the phone was still downloading (on the plus side it did keep me from unplugging the phone until it was finished).

    1. I have had this problem 8 weeks now
      I've spent 10 hours on the phone to apple
      No hope
      No progress
      Hangs on sync
      Takes all music of iPhone 6 plus
      Created duplicate playlists
      Has been causing other Bar to dwell by 20gb
      Restored about 10 times
      Got 8.1.1 no better
      Might as well just give up
      Tried absolutely everything
      Taken books
      Videos tv off
      Greyed out circles on everything
      CoMplained too Apple in cork
      Not even had a reply !
      Please help someone !!!!!

  5. After updating to iOS 8.1.1 it at first did not seem to resolve the syncing issue. But the next morning, when I sync’ed again, all dotted circles were gone. So for now, it seems as if my issue has been resolved. But this lack of dependability is a problem I think.

  6. Off the record:
    While my 4s does sync OK now it uses ...time...
    Funny thing, I have a cheap HTC ( to avoid roaming during traveling with a local prepaid SIM) It has a 32Gb micro SD. It syncs way faster than my 4s.
    How is it possible that an Android device syncs faster than iPhone 4s with a Mac? Someone at Apple must raise eyebrows...

  7. Just want to say THANK YOU! After my upgrade to 8.x.x mine was broken.

  8. Now have iOS 8.1.1 (12B435) and Yosemite 10.10.1 and iTunes The main change was the updated iOS. After having more than a month of grey circle missing songs, missing audiobooks, and bad sync issues; having done several complete restores only to have it revert to the problems a few days later — Now, FINALLY, (knock on wood) the problem seems to be solved. At first my heart had that sinking feeling (instead of syncing feeling) when upon installation of the iOS 8.1.1 update, the dreaded grey dashed circles reappeared and the artwork was missing and audiobooks missing. I thought, here we go again and was getting ready to have to do another complete restore. With nothing to lose, I thought I might as well try syncing once more and voila! All was correct. It took a while for this sync to complete, but all was well at the end. Hope it stays that way now. Good luck to others.

  9. What's frustrating to me is that mine aren't duplicates! They are different tracts in an audiobook so deleting duplicates is not an option.

    1. Did you upgrade to iOS 8.1.1? I had a similar issue, but once I upgraded two nights ago, after having some trouble upgrading, it finally fixed my issue with duplicates completely.

  10. My iTunes will either hang or crash when I'm syncing with my iPhone 6. In fact, it also hanged when I was updating my iPhone 6 to iOS 8.1.1 and I had to disconnect my iPhone 6 and do a restore! My problem doesn't seem to be with duplicate songs. I have an iPhone 5 and an iPad mini 2, which I sync with the same MacBook. Both those devices never had any problems syncing or updating; only the 6. I realised that the only difference in setup was that with my iPhone 6, I had selected "Sync Only Checked Songs". I have since unselected that option and my iPhone 6 seems to be syncing well with iTunes now. Keeping my fingers crossed that iTunes doesn't hang or crash again. Hope this info is useful for you guys.
    By the way, Apple products (both software and hardware) just doesn't seem to be as reliable as when Steve Jobs was around. Not sure how much longer I'll continue with Apple products if they continue to give me so much trouble.

    1. Jeffrey, I totally agree with you. Steve Jobs would have never allowed this debacle. I think Aplle's infrastructure is broken. I have an iphone5, ipad3 & Mac mini, & was going to upgrade all of them but they haven't made anything I want. Want more battery life, better front facing speakers , USB 3 & waterproofing. Instead like some weird cult they keep making things thinner & cheaper to make with less functionality. The Mac Mini was gutted- no quad core. There are products they make & I want them but they seem too expensive- iMac Retina & Macbook Pro Retina. Now with all of their software bugs, I'm not wanting to stay in the ecosystem.

  11. Mine was working fine again until last night. I'm using a very stripped-down playlist and after the 8.1.1 update I was considering changing back to the way I used to sync. I had been having problems with skipping track on a CD I had ripped, and re-ripped it outside of iTunes and added the files to the library, deleting the original ones. The original files were still on the iPhone, and in the past when I synced it would simply swap out the old for the new.

    This time it didn't work that way at all. The new files were never loaded onto the phone and showed the dotted circle in the playlist on the phone. The artwork for all of my albums was again deleted from the phone. After several unsuccessful syncs, I eventually gave up in frustration and manually deleted the the album on the phone and tried again. It never successfully loaded the tracks and the artwork has not been restored.

    Something has definitely changed for the worse in how iTunes manages syncing. I've never had these kinds of unresolved issues since buying the original iPhone

  12. Guys, Ladies, IMHO there is something wrong with what you're doing...
    My suggestion / solution is to restore iPhone or iPad to factory settings and sync as a new again. There might or is something wrong with earlier syncs. I know, a pain in the ***. I think it will solve your problems, as it has done for me. The first crappy 8 iOS update took me many painful useless hours, see this blog for many more comments...
    But believe me, the new OS 8.1.1 works... At least as far as I can see, with everything... Also the sync, as long as you give it ...time... time...time...
    It is absolutely not a customer fault or faulty hardware (the last statement of course with reservations), it is Apple that does not implement their updates, firmware or software right. So, in this case, a big boohh for Apple. Me being a former M$ developer for many years, I got used to these kind of..... (fill in anything), but Apple, always good, never ever necessary to troubleshoot, always 'works', never blue screens of death, be aware for the many, many, unsatisfied customers! This is not the Apple that once was... What the 'bleep' is going on...? Hello Tim... Hello Mr. Cook, do you or your staff read these posts..? What do YOU guys think...? Sincerely and big thanks to Rob to make this blog possible!

  13. That is the problem? Duplicates? The Fuck?
    Also something else that's been driving me mad, when I have different songs from the same album but two different sources I can't seem to merge them any more. Say I downloaded 3 songs off itunes and ripped the rest off my CD. Usually they'd have different info and I would simply change the one to match the other and tadaaa, they'd save as one album. Now, it simply doesn't save the change. Is the only solution now "hiding" my purchased songs in itunes?
    I'm about to use my 10 year old mp3 player again. This is no fun.

  14. I'm at a loss. I've done everything suggested with regards to "duplicates", I've wiped the phone, I've set the phone up as new one, and I'm still tearing my hair out. At best, I've had it sync flawlessly for three weeks. I had an issue with artwork and changes to playlists not syncing on Wednesday, but I let it sync again on Thursday morning and it eventually fixed itself. Thursday evening I made some changes to playlists and let it start syncing. When I woke up Friday, it was still waiting for items to copy and claimed that I had 90+ GB of "other" on the phone. Attempts to sync now result in a warning that there is not enough space on the phone, and the only way I've found to fix THIS problem is to wipe the phone, restore from backup, and sync 90+ GB of music all over again.

    Sorry, this in NOT user error. I have been syncing an iPhone ever since the first iPhone and have never had these kinds of issues. I bought the 128GB model so I could carry more of my music, but I've ended up syncing less because of the constant threat of having to reset the phone and do all over again.

    Based on what I've seen fore other uses, the Apple support engineers can't even get their story straight. Now we've got someone in the Apple support forum claiming that they blamed the problem on virus software! I'm totally frustrated.

    1. Wow!! an Apple employee accidentally erased my customized iTunes playlist by placing it in another folder because it wouldn't sync to my iPhone 6. I want to recover those play lists from my external hard drive. Is that at all possible? Or do I have to rebuild all new one?

    2. Jeff: My newer post mentions a second issue—incredibly slow syncs are a second known issue. Sounds like that's what you hit with the "waiting to copy." I was there, too, and only another restore fixed it.

      The huge "Other" apparently crops up after unsuccessful syncs (sometimes, but not always). Mine went away with the 8.1.1 update. Other than that, the only suggestion from Apple was yet another restore.

      A very frustrating experience for those of us experiencing these issues.


      1. Absolutely, do you think the geek squad at Best Buy can help? I just want to get my play lists back that should be in the external hard drive.

      2. Thanks Rob. I am on 8.1.1 but this will be my first restore under that version. Perhaps this will be the time that everything "just works" and will remain that way. Unfortunately, restoring a 128 GB iPhone is an all day task.

        1. There was no improvment after the first go with my computer, I tried to get money back but could not. I then would like someone to try and fix things for me again. Many problems.

  15. Very similar experience here--interesting twist. In our case, besides the 8.1.1 resolved large "other" and the duplicate song issue, we also experienced incomplete syncs due to bad disk sectors in just a couple of songs (apparently when it hit the bad sectors it quit entirely--and silently--rather than moving on to the next song). Some quality time with SeaTools flagged the bad sectors and sync is working again (new HDD on the way just in case).

  16. I've done it. I figured it out. I've had issues ever since I got my iPhone 6. Finally, I believe I've found a remedy.

    After reading your article on duplicates, I went through my iTunes library to get rid of any duplicates. I went through and resynced. It didn't work. What I did next was I unsynced all my music on my phone so that it was only the songs I had bought through iTunes on my phone. After going through my songs, I noticed that most of my songs were not downloaded on my phone but I saw that about 5 of them had been downloaded. After I "deleted" them (from my phone,) I resynced my phone with all my music. Worked like a charm.

    While it may not work for all, the fix worked well for me. I'm rather disappointed at Apple for releasing such a large bug without any notice. I'm still not satisfied with the overall experience, but I'm glad I could find a fix.

  17. I have to say that sync between iphone and iTunes is the mess. I have about 10k of songs that I sync and basically every week I run into some kind of issues that ruins everything and forces me to wipe up the whole device. It's hard to find what causes the issue but I think there are many of them. I cannot really find any solution on net to fix it. I think iphone or iTunes must keep some kind of "status" file that the sync checks to find out what is the delta to sync. I would like to force the application to check that from scratch because I think it's getting corrupted after few syncs. Do you have any idea if such a file exists? On the other note I just got my sync corrupted and this time it happened after I did one thing. Maybe someone could confirm that this is constant behaviour? I sync based on the set of playlists selected in iTunes. I removed manually from iphone few songs that are on the sync list. Next time I sync the songs are not back on iphone and the whole process takes hours (the previous sync before deleting the songs took under one minute)

    1. Just to add to my previous post.
      Assume I have 5 songs of artist1.
      I delete 3 of them (on iphone)
      when I go to artist list I still see Artist1 5 songs (in the list)
      When I go inside Artist1 I only see the 2 remaining ones.
      Like I said next sync (or the subsequent one is slow) and now all my Album Arts are gone and sync doesn't work anymore (example if I add new playlist to the sync list doesn't work)

  18. That worked great for me on my iphone 6, thank you! I had wasted hours trying all sorts of 'fixes', finally sorted. Cheers again!

    1. Hey Rob what worked to make ur IPhone 6 sync like its supposed to? Because mine still won't sync. Despite uninstall & reinstalling ITunes.

  19. This is CRAZY! We have to spend HOURS on a workaround because Apple released a product that doesn't work in the most basic mode: copy my music to my iPhone. Really? Learned about this while flying home and realized most of my music was not downloaded. My whole house is Apple; Now I'm ready to throw them all away. Seriously? You didn't test copying songs??? REALLY?? I will find Mr. Cook's email and sell my (considerable) AAPL holdings.

    1. I am devasted, fed up& lost for words....
      After 12 hours on calls to Apple . An unacknowledged formal complaint in writing I am still in exactly the same position
      No sync
      No songs
      What next I ask
      Whatever next

      1. It's gotta be a bug of some sort in the program. Possibly in the new IOS 8. I never had syncing problems before. The apple employee had the nerve to tell me it's a Microsoft problem. Just because I'm operating from windows.

  20. The issue with iTunes failing to complete syncing is not restricted to purchased songs or to any attached device. I have all my CD music imported to iTunes and yes there are duplicates as artists always cram the same song onto multiple CD's. I have been trying to re-sync my Apple TV (One) for over a week. iTunes will start syncing music and when it hits a duplicate song it will silently stop syncing even though all the status messages say it is still syncing. The work around is to close iTunes, then restart iTunes and start the sync process again. After a week I have about half of some 7,000 songs synced to my Apple TV (One). As far as I can tell this bug was not in any previous version of iTunes, but it sure is here now. Apple please fix it and let's get a stable version of iTunes released and leave it alone.

  21. This thing is a nightmare. At first I noticed some songs were missing from my phone, so I went to iTunes to see that for some reason there was a grey loading circle beside them when I tried to autofill, then later on the list grew. So I decided to delete all the music off my phone and try re-autofilling all the music. Worst decision I have ever made because now every single song in my iTunes has this grey circle and nothing will go into my phone. This is also affecting me when I try to back up my phone or sync it because it just pauses at the very end where it would say "step 4" and just sits there forever. Now aswell the songs go into my phone but aren't detected by itunes and just have a red circle and square around them. Someone please help with a decent solution to this problem which will actually work.

    Is there going to be a real solution to this problem besides completely wiping my iTunes and downloading every single song again which might not even work. I have honestly looked everywhere for a solution and it seems that everyone has a different one which doesn't work for most people.

    Are iTunes/Apple working on this problem or what? The problem happened for me the second I updated my iTunes so its obviously iTunes that's the problem.

  22. I have been laboring with this problem for about a week. I would try to synch a playlist only to find that while the process indicated it had completed properly it had not and I was missing stuff.
    It got worse. Tonight I started getting the freeze problems others have reported. I am also getting random indications of storage on the bottom of the iTunes synch screen I should have about 5G unused on a 32 G iPhone 5. It swings up to show less than 500 meg and then back again.
    Here's how I fixed it. I ended up deselecting all my music and audiobook synch selections, then synching the phone. Then I reselecting items I wanted and re-synched. I left off the audiobooks and this might be where the dupe issue was manifesting itself. However those books have been on my iPhone for a long time so not sure why this is suddenly the apparent problem. Anyway I agree with an earlier comment, Apple used to be bulletproof but not any more. I've been a user since my first Apple IIe: very sad.
    One other point which may be unrelated but since this problem started I have noticed that my phone does not connect reliably to my car audio through the hard wire connection. The phone will freeze if I fast forward using the steering wheel controls.. I also notice an indexing problem (tune being played is not the tune displayed on the car radio system). I did some tests and this does not happen with either of my two iPods, only my phone.

  23. This is not the first time my iPhone has made huge sync problems. For those who are not Apple-phanboys: why not try an Android smartphone the next time? (Mine is a company phone so I cannot choose another brand).
    Once Apple was famous for their user friendliness - but those days are long gone...
    My friends with Samsung phones have MUCH smaller problems compared to iPhone: wish I could switch.

    1. I believe the issue are not with iOS or the hardware. The issue for me is the Windows versions of iTunes. I've had four versions of the iPhone since it was released and two versions of the iPad all performed near flawlessly. But iTunes is another matter. Apple just will not leave it alone. With each new release there is a new look and feel but no improved functionality and certainly less stability.

    2. Two reasons:

      1) I cannot stand the Android OS. I've tried, many times, and it just doesn't work the way my brain works, or something. I find it a disorganized mess of an OS. But that's a minor reason, as I'm sure I'd get by if forced to learn.

      2) I do not want to run an OS that's devoted to selling information about me and my usage habits. If I'm going to be locked in, I'd rather be locked in to a company that wants to sell me stuff, instead of to a company that wants to sell me to advertisers.


  24. The iTunes stop syncing problem is not related to music alone. I have the same problem with iBooks on iPad Air. I have several hundred iBook titles some by the same author. iTunes will sync books to the second title by the same author and stop. It says it is syncing but it is not. I've not found a work around for this other than deleting all second titles by the same author. I have become very frustrated with iTunes. We have not had a stable release in over two years since the iTunes 10.xx series. Is Apple management listening? Is anyone testing the software before release? Is anyone supervising the software department?

  25. i think my glitch is that i had duplicate copies of that stupid U2 song.... except i deleted it from itunes but it still shows do i get rid of this?

  26. THANK YOU SO MUCH FOR THIS! Couldn't find the cause of my problem anywhere in the regular boards, and this is it exactly. What a super hassle.

  27. I see plenty of DUPES reported as similarly named tracks from audio book CDs I have ripped. Chapter 01a Chapter 01b same artist, same album, same release date, etc. Huge workload to try and "reconcile" these near-misses. and the $15 app is IMHO a bit steep to resolve this. I CANNOT sync music anymore via itunes, but must "manually manage." I added a ringtone the other night, and lost all music from my phone. Gotta drag and drop manually to repopulate the phone.

    1. The problem should only manifest itself with true dupes: same song number, album, artist, etc. In my case, they were updated versions of old purchased tracks. Some ha more metadata, some had differing lengths, but they were all true dupes.


  28. I have the same general problem but with failing to sync RCP Ringtones. iPhone 6 Plus, IOS 8.1.1, iTunes WTF. Copying and/or syncing tones from iTunes to iPhone is a basic function. Does Apple not test *at all*?? With every release, iTunes loses useful function and gains bugs. 12 is pretty useless.

  29. i selected the "show duplicates." it showed 4331 songs. after scrolling through the entire list that was shown, i could only find about 50 that were actually duplicates.

  30. That's S.O.P for them. Windoze blows, but I have many of these same issues on OS X Mavericks since going to iOS 8.x and iTunes 12.x.

    Windoze Is *NOT* The Problem!

  31. Damn I hate this f...g iTunes. My phone is doing same thing. Lost all the songs of the Eagles on the phone but they are all in my playlist on the library of hard drive. Tried dragging and dropping from library into the phone playlist it won't go. Only 4 songs of the Eagles out of the 105 of the iTunes library playlist are on the phone. This sucks. Every friggn time, I have to go through some B.S. on iTunes. And Apple never acknowledges it or does anything about it. They have had that problem with the exclamation mark on songs that mysteriously show up and disappear on the hard drive since iTunes was launched and never did fix it. F...Apple. My phone contract with AT&T ended 2 months ago and I'm taking this 5S down and getting an Android. Screw Apple.

  32. I think my issue is related to this, but relates to photos rather than music.
    I am a photographer and have about 7000 photos that I keep in a seperate folder and sync to my iPhone 6 and iPads 1 and 4. About 2 weeks ago (I think after an iTunes update) I noticed that about 100 photo were missing, including some that were previously synced. When I highlight the folder to sync, iTunes just cannot "see" these missing photos.
    I've tried deleting the iPod photo cache and rebuilding it, but this makes no difference. I'm pulling what's left of my hair out!
    If anyone else has experienced this, I'd really appreciate any advice you could offer.

  33. This maybe has something to do with the Genius playlist. I'd never had the problem before, but I enabled the genius playlist a few days ago. Last night, I loaded a several new songs, and tried to sync. Lots of old music disappeared, with grey titles marked with the "red circle". I just disabled genius, and now 1717 songs are syncing.

  34. Anybody out there tried the new iOS 8.1.2?
    Do not want to update yet, 8.1.1 is working kind of OK so far (but VERY slow syncing)

    1. I've updated, and was able to sync a bunch of songs without any issues.


  35. Thanks Rob, downloading now, server kind of busy; 5 hours remaining:-) Will keep posting...

  36. Had been trying for 2 days to synk my iTunes and playlists. The following finally worked. I Removed all duplicate songs from iTunes, then went to settings/general/....scrpll to bottom and RESET...."Erase all content and settings (scary). Restart iPhone and do new setup. Keep wifi sync OFF keep iTunes Match OFF. Hey presto it works

  37. Hi Rob, and all others who read these posts...: I updated to 8.1.2... So far happy as a clam! See one 'bug' (could be my fault... did not yet thoroughly check) I have one genre (christmas) that I added for the season, all 141 songs are also in a playlist. But: in genre it says 141 songs but shows only 40. In the playlist 141, all visible... Well, I can live with that, will delete them from iPhone in 2 weeks! And... Sync is now very fast! I do not understand that Apple states that the only thing fixed was ringtones and some minor bugs. Finally, 8.1.2 (for iPhone 4s) is back to what is was prior to iOS 8... Thanks Apple, and Rob, again thanks for this blog... Cheers and happy holidays!

    1. I thought my syncing issues were fixed when my new songs from the week synced w/ no problems. However, after spending an hour trying to get my podcasts on my phone to match what I have on the computer (ie what I've listened to, and no I don't want any of them saved) and adding artwork to 1 album successfully in iTunes (showed up and everything), added a playlist and then correcting track order on a personal album of mine - everything looked beautiful. Sync went through - took another hour - but not one single change I made transferrd to the phone. I did 3 more syncs each went by super quick. Still not one single change to my phone. What's the point???? So upset. These are only little things but they're emblematic of a larger problem that clearly apple doesn't care to fix.

  38. My problem is a little different, but possibly related? My phone still has my music on it but it will not sync with the cloud. My iPod, however is another story. It is an older model and is not bluetooth compatible. I've always just plugged it into my Mac and the synching happened. Now, in my futile attempt to get it to sync, 1) all my songs have been erased and 2) when I plug it in, I'm being given a message that sync is complete when, in fact, nothing has happened. I'm afraid to plug my phone into the computer for fear of what could happen to my music. How can I get music back on my iPod?

  39. I had the same problem. Lost over 600 songs when transferring from iPhone 4s to iPhone 6 plus ios 8. Made an appointment at the Genius Bar in Canberra and got told by a head genius guy that it was obviously an issue with my PC and nothing to do with ios. As you can imagine I wasn't happy as the same issue had occurred about 18 months before following the last major iTunes update. I then spat the dummy and went home and purchased Sharepod for around $22AUS. This allowed me to take my intact library off the 4S, transfer to PC and then sync to my new phone which I Had reset for the third time before doing this.
    As I had been told by the genius, not so genius guy!!, that the problem was my PC and corrupt files, it was immensely satisfying to have all my songs fully restored to my new phone.

  40. Found a solution that worked for me posted on igeeksblog by Ian

    Go into settings>music on your device and turn off the 'Show All Music' option. Works a treat..

    Now, that worked for me with the iphone attached to iMac in iTunes. Toggled the setting on my phone to ON , as mine was already set to off and synced and it went through and sorted it all out - Magic!

  41. Hi All,

    My long battle with iTunes is over. I figured out the secret formula to managing my 5000+ track library of iTunes and non-iTunes tracks which has the following benefits:

    - Makes it easy to manage your library as you upgrade from one Apple device to another.
    - Avoid the dashed circle problem in iTunes and the duplicate tracks that appear and disappear on my iOS device when syncing in iTunes.
    - Easily fix the tags and album art in all my tracks.

    1) Like most people, my collection of albums has both iTunes and non-iTunes content. My advice is to keep these libraries in separate folders on your PC, and I'll explain why shortly.
    2) If you're seeing a lot of dashed circles in the iTunes "On My Device" Music library, you may have tried to sync the same track to your device from different iTunes libraries, or perhaps by deleting and re-adding the same track two or more times from your iTunes library and syncing it multiple times to your device. iOS seems to keep track of each time a track is synced to your device. During the sync process, you may notice multiple instances of the same track in an album for example. iTunes eventually deletes all the duplicates, but it makes the sync process take much, much longer. Also, if your sync process is interrupted, it may result in duplicate or even missing tracks on your device. (Duplicate tracks can be manually deleted providing you set the right option in your device, but it is a pain because they will re-appear after you Sync again). It is possible to avoid all of these problems by following a few simple steps.
    3) Go into your iTunes library C:\Users\yourname\Music\iTunes\iTunes Media\Music and see what you have. Use file explorer to select all the album folders copy your entire library to a different directory.
    4) Uninstall iTunes completely from your PC. Go into the C:\Users\yourname\Music\iTunes and delete it completely (the uninstall process leaves it behind).
    5) Make sure you have backed up your device to iCloud. Re-set your device, deleting all content and resetting it to factory settings.
    6) Restore your device from iCloud and go through and set it all up again like you would if it was a new device. Notice that iOS restores all the iTunes content perfectly to your device with no duplicates, all the track and album art is in place. Its nice and clean at this point because Apple does a good job keeping all of the meta-tags and album art pristine for the content it sells. Let it finish syncing everything you purchased over WiFi.
    7) Install a clean copy of iTunes. Notice that after you log in (if prompted), your iTunes music library will also have every track and album (and music videos, movies, etc), that you have ever purchased (provided, of course, you haven't hidden purchases in your account. This is a separate topic, but you can fix that under your Apple account in ITunes in "Account Information"). Until you play a track or album, iTunes displays a little cloud in the corner of the album. This means it is purchased content that hasn't been downloaded. Don't worry about it, because we're going to overwrite that content from your device which has the exact same set of content at this point. Don't connect your device yet!
    8) This is very important. Go into Preferences, Advanced. Check "Keep iTunes Media folder organized". Uncheck "Copy files to iTunes Media folder when adding to library".
    9) Connect your device. Click on the little iPhone icon and look at the Summary page under Settings, Summary on the left. Leave all options under Options unchecked, including "Manually manage music and videos".
    10) Click the Sync button. You will be prompted with a message that says your device has a different library than your iTunes library and would you like to transfer your purchases, etc. Click the affirmative option. After the sync process is complete, your iTunes library will be the same as the library on your device. Both your iTunes library and the library on your device has everything you purchased in the iTunes store and nothing more. No more duplicates, dashed circles, or any other artifacts. Nice and clean.
    11) Next, go into that backup library you created that probably contains all of your previous iTunes content, plus all of your personal tracks and albums which did not come from iTunes. Create another directory which will only contain your NON-iTunes content.
    12) This can be tricky. If you have a lot of albums like me, it can be hard to remember which was previously purchased from iTunes or which was obtained from a CD or other source. Open up several file explorers and refer to your iTunes Music folders as a reference to what is purchased. Create that clean directory from your back up and make sure it doesn't have any of your iTunes tracks.
    13) Next, take this time to clean up the meta-tags on your non-iTunes content. I use a great program called MusicBrainz Picard. I know it sounds funny, but its a great, non-fussy tool that makes it easy to fix your tags automatically. Use it to fix any of your tracks that have missing title or artist info. Add files to it, scan, and click save to automatically fix the tags and download the correct album art. This really makes your library a lot easier to use once it is loaded into iTunes and device.
    14) OK, now that you have a separate directory with all of your non-iTunes tracks which have been cleaned up with MusicBrainz or whatever utility you use, you're ready to carefully add your non-iTunes content into your iTunes library.
    15) Remember, you have previously unchecked the option "Copy files to iTunes Media folder when adding to library" (double check this option now). Go into iTunes and click Add Files to Library. Navigate to your non-iTunes library and add each album to iTunes ONE BY ONE. I know this is a pain, but it seems to be the only way to do it. Your iTunes library will be pointing to iTunes content under the iTunes folder structure and everything else in a separate folders structure from where you just added it.
    16) One option that is available to add tracks to your library is to copy them into a folder in your iTunes folder called "Automatically Add to iTunes". When iTunes sees content there, it moves it into your library. Don't do this! The problem is, you are adding iTunes and non-iTunes content together in the same folder which is going to be hard to manage if you every need to clean up your library and re-install iTunes. Remember, KEEP YOUR iTunes content separate from your non-iTunes content. This means it is in the same iTunes library, but it is kept in separate folders. Have I mentioned this enough?
    17) After adding all the non-iTunes tracks, notice your iTunes library has a clean copy of iTunes and non-iTunes content. You're ready to Sync your device.
    18) Sync your device. After this, all your non-iTunes content is nicely co-mingled with your iTunes content. There are no duplicates, no dashed circles in iTunes. Life is great!
    19) As you browse your device library, you may run across some content which has not been downloaded. It will display a little cloud with an arrow. Simply click the cloud to re-download the missing tracks and they should stay put.

    Remember, keeping your non-iTunes folder structure separate from your iTunes folder structure will make it easy to re-install iTunes later if needed and avoid getting duplicate tracks registered to your device.

  42. Well, I've tried everything. Thanks to everybody for all of the suggestions, but nothing seems to remain stable. Eventually an issue arises with the music database and the phone refuses to sync. The best I've had is a month of good synching, but that ended when the dynamic playlists stopped updating and content that should have been removed from the phone remained on the phone. After that, endless time spent in a sync that accomplished nothing.

    The only thing that works is wiping the phone and starting over again. Whatever Apple changed with iPhone syncing broke something that's worked perfectly for me for almost ten years.

  43. I am dealing with the error -54 bug right now itunes does not state their is any duplicates even though there was I went through my list and deleted some I have the grayed out circles my question is for somebody on the duplicate songs is the songs by the same artist or can they be by different artist I noticed with my
    CHRISTMAS song list I have a lot
    Of same songs by different artist
    This bug is getting to be a pain I am trying to set my iphone 5 up on a new computer and this is going on have the latest
    Software 8.1.2 and the latest itunes Any more advice please

  44. I have been having trouble syncing lately as well. I had to restore TWICE because 40+ GB of 'Other' is being synced to my iPhone 5 for some reason?! I'm giving it a month or two before I attempt to sync again.

    I thought it was a corrupted file, but all of my music is either ripped or purchased through iTunes.

  45. I had a happy ending.
    My music stopped syncing (about 1900 songs on device) and my device started losing songs. Fixed it by upgrading to 8.1.2 and removing and re-syncing my music. Didn't have to wipe my entire device. Don't know if 8.1.2 alone would have fixed it because my actual steps were:
    1. Uncheck sync music. That didn't seem to completely succeed but not sure because iTunes and the device reported different songs on the device!
    2. Upgraded from 8.0 to 8.1.2.
    3. Sync'd again (with Sync music still unchecked.) My device only contained music I'd purchased on it.
    4. Checked Sync Music and sync'd again. Took a while (1909 songs) but wasn't "slow". Seems to have worked great.

    My library has been around a long time, so it's quite possible I had the duplicates the original poster did. But never made any attempt to delete them, just upgraded to 8.1.2 and re-loaded my music.

    The other takeaway is that I didn't have to restore my entire device. Your mileage will undoubtedly vary.

  46. Not sure that it's only duplicate songs. I recently bought a few CDs and decided to rip them onto my iTunes library and get them synced to my phone. After going through the ripping process I started the sync. The same thing happened as was described above except that the sync finished for every song that was bought through the iTunes store. All of the CDs I had ever ripped now had the little grey circles and were not playable on my phone though they continued to play from my laptop with no issue. Not really sure if its the same problem but I had a ton of CDs burned so my playable library took a significant hit. If anyone can help me with this I really would appreciate it.

  47. I Had This Same Problem (29 Items Couldnt Sync On Itunes Blah Blah).....I Resolved My Issue WIthin a Couple of Seconds, I Turned Off My Iphone 6 (While Still Plugged In The Computer), Let It Stay Off For a Couple Of Seconds, Turned It Back On ..My Music, Playlist (That I Had On My Iphone) Were Still Checked Already So I Clicked on "Sync" & It Begin To Sync ! ..Sorry For Anyone Else Who Is Having This Problem, I Thought I Was Going To Go Crazy Lol Any Questions Please Feel Free To Ask! Merry Christmas Everyone <3

  48. I purchased two albums and then synced and some of the songs were transferred to the iPhone twice, so mine isn't a case of purchasing the songs twice. My screen looks like yours with the little circle on the left, but they are the exact same songs on their twice. If I go and view duplicate songs, it's greyed out. But, they really aren't duplicates on my PC, only on the iPhone.

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