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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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Question marked as Top-ranking reply

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 20, 2014 2:14 PM in response to medora66

Like @medora66, I was in touch with a senior advisor and had my case escalated to the engineers. They stopped following up on it after I resolved my issue with deduplication. However it's disheartening to get the impression that apple is not in sync (pun acknowledged) on it, as the following are all true:
*Multiple people have reported the same issue to senior engineers

*Multiple people (including me) have sent the thread to THIS CONVERSATION to them

*Another post (in this thread, I believe) goes into detail about the duplication problem, the tool to fix it, and the idea that APPLE is aware of it.


I don't know about the rest of you, but I would have been much more comfortable over the last month if Apple had simply said: Yes, we are aware of it, and we are working on a fix. The silence, instead, is deafening.

Oct 20, 2014 2:58 PM in response to matt4692

Well I don't have the time to trawl through my music library looking for duplicates.

I know I have plenty from Michael Jackson (from his original releases and greatest hits etc).


I've never had this problem with the iPhone 4S. Apple is well known for releasing products that 'works' out of the box. Well with the iPhone 6 we have to jump through multiple hoops to get a compromised working product.

Oct 22, 2014 6:54 AM in response to matt4692

I actually had this problem on my Iphone 5 but was still annoyed to see it again on the new iphone. I've just upgraded to Itunes 12 so thought that might be the issue with my Iphone 6 not syncing properly. Anyway this is what I did and it worked:


1. Go to the summary tab for your iphone on Itunes.

2. Uncheck boxes which say 'Automatically sync when this iphone is connected' and 'Sync with this phone over wifi'

3. At the bottom of the screen you should have a button with 'Apply' on it. Click it.

4. After a couple of minutes your iphone should start syncing.


Note: I had my music in playlists rather than just sync all music. I had the ghost tracks originally and itunes was saying they were on my phone. This fix changed them from ghost tracts to actually existing on my phone. I uploaded 45gb.


Hope this helps!

Oct 22, 2014 11:15 AM in response to matt4692

Crikey, this got really complicated; here's my ten pennies worth.


On my iPhone 5C, because I only had 32GB storage available, I'd only chosen some 62 of my 200+ playlists to sync; this worked quickly and perfectly.


Now I have an iPhone 6 (Plus - not sure it matters a whole heap), with 128GB of storage and which I set up from my 5C's backup. This went fine.


Then, because I now have the space for all 39+GB of my music, I selected "Entire music library" and pressed sync.


This took a long time, and once it had finished, I checked out what had been installed on the iPhone; this was the original 14GB of my selected playlists from the 5C; even though I'd asked for all my playlists. Too, because iTunes, poor thing, seemed to be really confused, possibly about the conflict between some playlists and my later instructions for all, the sync process went on, and on, and on. With no satisfactory result.


I checked in thee forums, and noticed a lot of people suggesting pretty much everything, some solutions which worked and some worked for some people, but not for others. I didn't try any of these solutions; my solution was, somewhat drastically, to deselect all the playlists I'd originally selected for my 5C, and which were stubbornly being applied to my 6, and then just selected one playlist which I knew only had one song in it.


Then I hit sync again, but the coloured bar at the bottom showed I still had 3000+ songs on my iPhone. The sync went on for a long time, with nothing apparently happening; one sad iTunes just kept its wheels spinning, trying to figure out which instruction to follow; in the end it was taking so long, I force quit iTunes, which was not a comfortable idea.


Having left the screen with, apparently, my 3000+ songs on my iPhone, after I reopened iTunes, lo and behold, I only had one playlist on my iPhone.


I then, bearing in mind that I'd force quit the last time I was in iTunes, did a sync, and this went through very quickly.


Progress of sorts.


I then select the "Entire music library" and dived for the sync button again. Once all 7951 songs (39+ GB) were transferred - this took a while - a subsequent sync went through without difficulty, and, more to the point, as quickly as could be expected, in about 10 seconds, which might be what to expect considering nothing had changed.


This worked for me, in that I now have all my playlists on my iPhone, it's just a pity that I had to jump through so many hoops to get there.


I hope this might help others in the same boat at I was.

Oct 25, 2014 12:27 AM in response to crliege

What appears to have worked for me is:


- sync with nothing checked/ticked - no photos, tv shows, etc.

- sync a single song, make sure it's working

- sync a few more, make sure it's working

- build up from there - perhaps then see if adding photos is the problem, etc.


Until I un-synced all other media I couldn't sync music properly.

Oct 27, 2014 3:22 AM in response to br3tto

I had this same issue, on Windows 8.1 with iTunes 12 and my iPhone 6 128GB. I tried every solution I could find to sync my music, but it constantly stuck on waiting for changes to be applied, or if it got to the next stage it would sit there forever saying copying song 1 of x and never progress. The thing that finally appears to have fixed this is using MP3Val to check all my MP3 files (http://mp3val.sourceforge.net). It found a fair number that had garbage at the end of the file, especially podcasts for some reason, but after fixing them all my sync is now working and I'm happy again! Seems either the new iPhone or new version of iTunes is a bit more finicky than before.


Anyway hope this helps, as it took me a fair number of tries to find a solution that worked for me.

Oct 27, 2014 10:46 AM in response to Martinboy1974

Thank you to Martinboy1974, for help with this fix.


Windows 7 Computer...Silver Verizon iPhone 6, 128 gigs...


I logged out of iCloud Control Panel

Uninstalled from remove programs in the control panel of the PC

Restarted PC


I manually removed all checked music (playlists, artists, etc.) from iTunes & hit sync.


I added all the music back. I synced multiple times after, added & removing playlists. it worked every time!


I reinstalled iCloud control panel & syncing still works perfectly.

Oct 27, 2014 11:04 AM in response to Martinboy1974

*** DISREGARD THE POST I JUST MADE *** Refer to this...


Thank you to Martinboy1974, for help with this fix.


Windows 7 Computer...Silver Verizon iPhone 6, 128 gigs...


I logged out of iCloud Control Panel

Uninstalled from remove programs in the control panel of the PC

Restarted PC


I manually removed all checked music from syncing (playlists, artists, etc.) from iTunes & hit sync.


I never needed to remove the actual music from the iTunes program. I synced multiple times after, added & removing playlists. it worked every time!


I re-installed iCloud control panel & syncing still works perfectly.

Nov 1, 2014 2:32 PM in response to yocko

I have the 128 gig 6 and am using a pc with windows 8.1. 1800 tunes mostly from non Apple sources, and yes, some duplicates, because I just reloaded my new computer and haven't had time to weed things through . I unchecked all music, closed itunes, the reopened itunes and checked all music. Make sure you go to your device and check the "sync music" box is checked. It then synced all 1877 tunes with no problem in about 15 minutes.

Music Won't Sync From Itunes Correctly

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