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Music Won't Sync From Itunes Correctly

I just bought the iPhone 6 yesterday (it's my first iPhone), and my music just doesn't want to sync correctly. I use iTunes and have about 1.6k songs. I'm plugging it in using the usb port and syncing just like I have with all my previously owned iPods. The issue with when I try to play one of my songs, a red square with a red circle around it shows up. This happens for about 70% of my songs and skips to the next available one. I then try to sync my songs again and different songs then become unavailable, while previously unavailable songs become available.


Some of these songs have been purchased through iTunes, some have not. Both seem to randomly not work. I'm wondering what the problem could be? I've never had this problem with my iPod.

iPhone 6, iOS 8

Posted on Sep 20, 2014 8:54 AM

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Posted on Sep 21, 2014 5:36 PM

Matt, I'm having the EXACT same problem you have described — with the red square and circle around it. I have about the same number of songs as you do. Everything was fine with my iPhone 5, and everything is still fine with my iPad Mini. The problem is getting the iTunes on my iMac to sync onto the new iPhone 6. So I think the problem is not iOS 8, but the new phone itself. I also have suspicions about iTunes Match, which I have never fully understood. I have turned it off (on all my devices) and tried doing a fresh sync to the iPhone, but I still get the exact result you have described. Hope they fix this soon.

199 replies

Oct 16, 2014 1:05 PM in response to SOULNATIONAL ARCHIVE

I'm not sure what a "prosedure" is, so not really sure where I'm questioning it.


But you are continuing to bully and troll (not the other people on this thread) because you seem to be taking personal offense that nobody is recognizing that you solved a problem. Do you want validation from all of us that you figured out your problem? OK, here it is: you're smart, good for you. Your phone works great? Good, run along and play with it. If you had bothered to read anyone's posts, including mine, we expect Apple to come to us with an official response for a problem that is impacting many, yet they refuse to acknowledge.

Oct 16, 2014 1:24 PM in response to SOULNATIONAL ARCHIVE

I am a neutral third party in this disagreement, speaking on behalf of MANY people whose email inboxes are getting cluttered as we speak. Can we please reserve posts on here for solutions/possible solutions despite how upset one could be about non-technical commentary? I do expect my inbox to be cluttered as I am following this thread, but would appreciate it be only as much as is necessary. THANK YOU.

Oct 16, 2014 4:49 PM in response to musicmanasp

I am now writing to share the solution that worked for me today. I am confident that it truly worked and that I will not have to take back this statement. I synced multiple times, with and without changes, over wifi and over cable, and each time was able to play all of the numerous random songs that I tested from different albums.
While I sincerely HOPE that this will work for everyone (and please like this post if it works for you), I of course understand that it is possible that similar/same symptomatololgy could be presenting for different reasons. Note that I haven't posted in a few weeks but like many people reading this, I have been reading every post on here every day, doing my best to synthesize that information as it applies to my situation and planning an algorithm with which to attack this problem.


Pertinent Factors:

  • Issue is with syncing my music to my new iPhone 6, 128 GB AT&T (space gray).
  • The first iPhone 6 I got in the mail from AT&T came with a screen defect; however, I set it up and used it for a while anyway before getting a replacement phone from the Apple Store. It is with this replacement that I had the problem, although I am not sure if I had the problem with the original phone too.
  • I named the replacement phone with a different name than I assigned the original one with the screen defect.
  • A brief summary of the problem is: the songs would appear on the phone after a sync but when I went to play one it would come up with a red play button next to it, rapidly skip to the next song where the same thing would happen, rapidly switching through songs with no sound coming out until it ended up on a song purchased from iTunes. Subsequent syncs would add/remove various numbers of songs almost randomly, but these songs were only SHOWN on the phone for the most part and would shuffle away as described when clicked upon.
  • I did previously have iTunes match, and it was off months before I placed the order for iPhone 6.
  • My initial attempts before finding this forum involved deleting all of the music from the iPhone (by going through the settings on the phone itself where it lets you ‘manage storage). No success.


The steps that fixed it permanently:

(NOTE: I made sure the only playlists I had were smart playlists... if you have regular playlists make sure that they don't contain any songs that could be duplicates.)

  1. 1) plugged in phone
  2. 2) changed the name of the iPhone within iTunes by double clicking on the name. I changed it to what I named the original iPhone 6 I received that had the screen defect.
  3. 3) Deauthorized my laptop (on which I was working with the phone connected)
  4. 4) Filtered all songs in iTunes for “Exact Duplicate Items” by pressing the alt/option key and clicking on View.
  5. 5) Noticed that there were ~200 (out of a library of over 10,000 songs) duplicated songs, many of which were actually voice memos (and on my iPhone I had noticed previously that my voice memos were screwed up in that they were all grayed out (inaccessible) and mostly contained the same title).
  6. 6) Manually located each duplicate song file (NOT in the iTunes music folder—I never ever touched that. Read on.). For a given song that was duplicated, it either had a space and then the number 1 appended to the end of its file name or a space and then a number higher than one appended to its file name, indicating there were in fact more than one duplicate. Additionally, some duplicate file names for voice memos, in addition to being as described above here in this paragraph, also had a different format as their file name that indicated the same time stamp information about them. Note that in every solitary case I was sure to (1) delete ALL duplicates, (2) delete the duplicated files and NEVER the original. Note that iTunes will NOT change in any way whatsoever until the deleted duplicate file has been deleted FROM THE TRASH. ** Make sure none of the songs in your playlists refer to duplicates or are duplicates.
  7. 7) After deleting the duplicated song/voicememo files from their original folder(s) and from the Trash as described directly above, I went back to iTunes where it was still just displaying exact duplicates. I double-clicked on the first song/voicememo, and pressed the >> button on my keyboard continuously, during which time iTunes would flag the duplicated songs with a “!” due to the fact that I had just deleted the duplicated files. I selected ALL of these marked with “!” and deleted them from iTunes.
  8. 8) I exited the “Exact Duplicate Items” view, closed and reopened iTunes, and re-entered “Exact Duplicate Items” view. I saw that no more duplicates of any kind existed in my iTunes song library (that included voice-memos).
  9. 9) I re-authorized my laptop with my iTunes account.
  10. 10) At this point, iTunes did not show my iPhone connected even though it was (which is likely not relevant to anything). So I unplugged and plugged in my iPhone. It was not set to sync upon being plugged in, so it did not sync at that point (obviously). I went into the syncing settings. I unchecked the option to sync ANY AND ALL music, a dialogue appeared warning me that upon next sync all music would be removed, I accepted that dialogue, and then I immediately re-checked the very same button (to sync all music). I did this same process for the option to sync any playlists.
  11. 11) At this point, I simply synced my phone and the problem was solved. (As stated above I verified that it was a true fix).



If this method works for you please spread the news clearly by referring to this method as "Method J".

Oct 16, 2014 5:12 PM in response to musicmanasp

I Know it's not the IPhone6 or name change reason. At least not in my case. I am running a 4s and started since the ios8 update. I rarely sync or change any settings in iTunes. I am going to do as stated above with de-authorizing and re-authorizing iTunes along with deleting duplicates. I will not sync until I see some feedback from other people as I have no need and all music available. I have a question though, not to jack thread. Anyone else having a problem with certain albums having one song out of the album. I think I have 3-4 albums, one purchase and 3 addes from CD's where the first song of album is separated from the rest of the album. I try doing the get info and making sure EVERYTHING is checked and the same and still does not correct this. Dont know if this is a possible prpblem due to or In conjunction with our current problem as well or different problem all together.

Oct 16, 2014 8:04 PM in response to matt4692

I'm having the same issue. iPhone 6 128GB in Space Gray.

I spent most of the night restoring from backup after wiping my phone.

Some songs still won't sync - I can see the songs didn't sync by going to the device, then clicking "on my device" and see a lot of gray circles.

I'm using iTunes version 12, but the same issue was happening with version 11.

I tried many of the suggestions here - removing duplicate songs, trying different methods of syncing, authorizing and de-authorizing my pc (Using Win7).

iTunes match is enabled on my pc, but not on phone (i tried several combinations).


This is a serious problem.

Oct 17, 2014 12:56 AM in response to BacMan1031

Well this bug has now infected my previously immune ipad mini, and there have been no software updates during the interim period so I'm confused as to why it would happen now. The other new factor is that not only does it delete all my music, it also flips out when I play any tv shows and gives me the startup screen before returning to the previous state as if nothing had happened.

I have no fixes, but I do feel it's important to document these events, if anything to avoid having to laboriously state the same sequence of events over the phone to an applecare advisor; this way we have all our troubles documented here for ease of reading.


I have a macpro en route to me (yes, despite the buggy launch of the 6 I am still a fan of Apple products) and once that shows up I guess I'll be able to test the new OS with my devices and let y'all know if that solves the problem, cos I sure as heck ain't upgrading my current mac until I know that shizzle is safe.

Oct 17, 2014 9:23 AM in response to Fraston

Problem description: only some songs that appear to be on the phone are playable. Many other song titles appear, but when I attempt to play them, the music skips to the next playable song, sometimes skipping past six or eight other songs, and the song that I originally tried to play now has a symbol similar to the one I normally see in the App Store when I am about to download the app. (It shows a thin circle around a square, all in red.)

. Note: I use a Windows 8.1 PC, not a Mac, to sync my iPhone 6.

. I have an iPhone 6, 128 GB, Space Gray.

. I had previously unchecked the box in iTunes that says 'automatically sync when this device is connected.' Now, it syncs only when I click 'Sync' or 'Apply' button, as the case may be.

. I had also previously performed a repair installation of latest iTunes version. I do not know whether that made any difference.

. I had also previously completely reset my phone, erasing all content and settings, and starting over. That solved the problem at the time, but it subsequently returned when I tried to add more songs to my phone.

Problem Solution:

Here is the exact order of the steps I took:

. I synced the phone without making any changes.
. (I would try skipping this step next time.) I disconnected the phone and deleted all of the music on the phone, using the Settings - General - Usage - Music - Delete approach on the phone itself.
. (I would try skipping this step next time.) I synced the phone again; that resulted in only 850 songs being copied to the phone, far short of the more than 4,000 songs that should have been copied.
. I disconnected the phone from the computer and iTunes.
. I reconnected the phone to the computer, and in iTunes, I unchecked 'Sync Music.'
. I synced again. That resulted in all of the music being deleted from the phone. Interestingly, all of the movies were recopied back to the phone. (I assume they were previously there, so that seemed strange to me. I had not clicked anything that should have affected the movies.)
. In iTunes, I checked 'Sync Music,' then clicked 'Apply.' That seemed to result in all of the music, more than 4,000 songs, being copied back to the phone.

. I have since confirmed that (probably) all of the songs I expected to find on my phone appear to be there, and are playable.

Of course, all of the syncing and resyncing took a long time, but at least all of my music was there.

One more comment: I have witnessed the 'waiting for changes to be applied' message being displayed for a long, long time. In my case, however, it subsequently appeared that something actually was happening while that message was displayed. In other words, although the message should have changed to something like 'copying,' or 'deleting,' those actions were indeed happening in the background. I was patient, and the 'waiting for changes' message eventually disappeared.

Oct 17, 2014 1:20 PM in response to gordoncm

i to see the exact same thing on my phone. It only occurs with music I've ripped from cd. The music I purchas from iTunes never gets removed. I discovered that it I attem to play those tracks and the music app skips over all the songs that aren't really there, when I connect my phone again iTunes will copy them back. I sure hope this is fixed Monday with 8.1 as itunes 12 has done nothing to address the issue although I origian thought it did.

Oct 18, 2014 9:32 AM in response to th3r3ds0x

Well, I was overly enthusiastic about the apparent Yosemite fix so I upgraded today and...well now the movies, tv shows AND music are all screwed on all devices. I might try deauthorizing all my devices, and then digging out my old walkman. I still have cassettes of Beatles albums, which is more music than the 2 ipads and iphone 6 currently. Reboot after reboot, erase music on fone, click all buttons in iTunes...my saturday has been a carnival of stupid repetitive actions. For the first time I'm actually beginning to regret buying this now, and that makes me very very sad.

Music Won't Sync From Itunes Correctly

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