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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 8, 2014 1:03 PM in response to Fraston

FRaston: so all of your music plays on your iPad mini? Mine also plays on my Gen 2 iPad BUT when I synced it last night, it said it was done syncing on my laptop but all of the playlists were flickering and spazzing out on the iPad! I went to "eject" from the laptop and it had the spinning arrow like it was still trying to communicate . Music all there though!



I haven't synced my iPhone for weeks now.

Oct 8, 2014 1:06 PM in response to skichick1968

What I did was in iTunes, I unchecked the top Synch Music box completely. I backed up so that all music was deleted. I then checked the same box. My settings are to check the sub-box " Selected playlists, artists, albums and genres", and I also check Include Music Videos and Include Voice Memos. I then selected manually the playlists to synch. I hit synch, and it seems to work completely.


By doing this, I got all of my music on perfectly. I have now done this several times now to test it, and to add additional music. It has worked for several days now.


Hope that this helps!

Oct 8, 2014 9:36 PM in response to matt4692

Just checking back in. I haven't synced my music since my post last week (which is highly annoying, in that I like to be able to do so - I have enough different playlists that it hasn't gotten repetitive yet but it will) and have had no troubles with the music in this time frame. Plenty of other minor aggravations that disappoint me in the aggregate, but nothing that is lighting my ire as this issue is. I'll try a normal sync this weekend first, when I have time to wipe the music off and replace it again if it doesn't work. I'll update with results and any observations when I do so.


I always wonder what an original poster feels, when there are so many pages of replies and no real answer, just more replies of “me too!” I know that I'm usually stuck somewhere between “thank goodness I'm not alone” and “why isn't there a blasted answer yet?!?”

Oct 12, 2014 9:46 PM in response to matt4692

I think I have a breakthrough in understanding the cause, if not the fix. Sorry this is a little long, but:


After I subscribed to iTunes Match, there were a few songs in my library that appeared to be duplicates of songs I already had, but where the actual song does not match the title. An example is the Jack Johnson song called "Flake".


The real song has a length of 4:40. Match put another song in my library identified as "Flake" from the same album, but with a duration of 2:26. That song is actually a different song from the same album, called "The News". I didn't have the song before, but iTunes Match seems to have put it on my computer and misidentified it as "Flake".


So here's where it gets interesting. If I sync all of my songs beginning with "F", EXCEPT the misidentified version of "Flake", everything is fine. But if I INCLUDE the misidentified song, blammo--the problem occurs again. And amazingly enough, as soon as I remove the fake "Flake" from the playlist, the sync works fine and all the missing "F" songs are replaced.


I have to go through my library and find where else this has happened. There are definitely other instances where iTunes Match created duplicates of songs I only had one copy of.

Oct 12, 2014 10:02 PM in response to Poiks

....probably why this is taking Apple awhile to correct. Because of the DRM-restricted duplicate content issues with syncing, what I did was moved all my AAC purchased and protected music dupes into the trash. I then was able to move 10,000 songs over to my new iPhone.


I Personally think the latest release of iTunes is real buggy as well. More than iOS 8. My iTunes has crashed several times trying to communicate with my iPhone.

Oct 13, 2014 12:37 AM in response to SOULNATIONAL ARCHIVE

it drives me insane. I am completely clueless.... this is also the reason i bought a 128gb iphone and nothing works. it mystifies me.... so i copied everything, deleted everything. the put it back on.... i saw the music transfer.... so all the songs are on my phone.... and then i play one.... and the iphone shows ALL songs greyed out with a download dot behind them and a in the cloud sign. (this is with itunes match off).


i had exactlt the same drama when yosemite came out with Sonos, it also suddenly couldn't acces the itunes library and only a handful of songs downloaded.


and now we get another apple announcement on stage with applaus and hopefully a functional stream, and this while last keynotes stuff doesn't even work...


THIS IS THE MAIN FUNCTION OF MY IPHONE it is not some little glitch that one day will be fixed. What surprises me that only 6 pages exist on this problem.... we must be in a small minority. but what is it that ties us together?

Oct 13, 2014 12:43 AM in response to yocko

Have you tried to find duplicates songs that may somehow be causing this (based on my previous post)? So far, getting rid of those duplicates seems to have fixed this for me, but I won't know for sure until I start syncing my whole library again, and see if all remains well. I'm not confident but will advise when that is complete. This is still an Apple problem--Match is duplicating songs, and in some case incorrectly, and it seems to make iTunes choke.

Oct 13, 2014 8:23 AM in response to yocko

perhaps we all have large iTunes libraries with anomalies & files that simply aren't cooperating. But if you search the internet, there's widespread issues, notably with syncing over wifi. A lot of people are having problems with iOS 8 and iTunes 11.4. And there's countless others who simply aren't putting this aspect of the music transfer to the test; i.e., they're buying music on their iPhone and don't have a computer... or made it by the sync luckily unscathed...or don't care...or simply aren't reporting the issues and listening to Pandora while this gets resolved.


Waiting for iOS 8.1 and iTunes 12....

Oct 13, 2014 3:24 PM in response to matt4692

I've had this problem since launch. Bought a 128 so I didn't have to carry my trusty 160 ipod in my car anymore, but its been more trouble than its worth. I've restored the phone probably ten times. I have got the music on it twice but it always gets corrupt and becomes blank data. Meanwhile, added a new album to my itunes today and hooked my 160 ipod up and it synced like it was no big deal. 97 gigs of music.

Oct 13, 2014 3:34 PM in response to matt4692

Here is a solution. It's not the definitive solution but for me it has worked until we hear something from Apple, you have to be an iTunes match subscriber . Restore your phone, do the sync all music and after that turn on music match and stay away from iTunes, it's terribe and sad but that's the way to have all your music intact and only adding new stuff via iTunes match. This is the path Ive choosen.

Music Won't Sync From Itunes Correctly

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