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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 15, 2014 9:01 PM in response to Poiks

Yea that's good info. I have roughly 5000 songs in my iTunes library. It's aboit a 50/50 split between iTunes purchases and music from my cd collection. I actually cleaned it up quite a bit over the weekend trying get this working. I did have a few duplicates in there but they are all gone. I have no idea if there are any rogue songs in there with bad info and I doubt I'd ever find them without the help of some sort of software tool. Can't wait until this is resolved. Something so simple has the ability to really wreak havoc.

Oct 15, 2014 9:05 PM in response to th3r3ds0x

One other thing I found is that I often had to delete music through the Settings / General / Usage / Storage / Manage Storage function, that tracks would stay on my phone even after unselecting their playlists in iTunes. This way I was able to continue to troubleshoot it over and over without doing a full phone restore.

Oct 16, 2014 8:26 AM in response to Poiks

this issue has nothing to do with iTunes, Match, iOS or the iPhone 6.


It does however, have everything to do with de-authorizing and re-authoring the devices on your Apple ID/iTunes account. Deauthorize your computer using iTunes


I too used this thread to complain and rant about how transferring should be a seamless no-brainer. Since I isolated the problem, I now have a perfect syncing iPhone 6 Plus, every song is transferred without needing Match or any other tweaks. I'm syncing over wifi, lighting cable, you name it. No errors, nothing.


But since most people don't actually read here anymore and just complain--or think they're smarter than most here--they continue to lambast the thread and blame Apple. It's a simple fix, people (and dare I say a rudimentary normal step the Apple Care staff would walk you through) .

Oct 16, 2014 8:28 AM in response to SOULNATIONAL ARCHIVE

Soulnational, with all due respect -- the responsibility in clarifying all this and ending this discussion lies with Apple. If what you propose is truly a fix, then APPLE should post definitively and say so -- and then they should inform every single tech -- every single person that works the phones and staffs a Genius Bar -- anyone that has any contact with customers, period -- about how to address this issue. The "rudimentary normal step" you mention was never suggested to me, and my case is now sitting with Apple technicians -- I've been through TWO senior Applecare specialists, countless "experiments" -- and countless hours of hassle.


I had this problem right before a vacation -- two weeks ago -- and returned to about 100+ emails in my account, notifications of different posts, solutions, etc. There are about 25 different "fixes" -- and about 50 different retractions ("whoops, I thought it worked but now I'm screwed again.")


I'm sure you are super savvy and you seem very confident about your fix, but -- how can I know at this point that your fix will work, when so many others posited here have ultimately failed? What if I try it and it doesn't work for me? And I have to start from scratch for the umpteenth time? It would be a full time job for me to read through this mess and figure out what the REAL fix is. And that shouldn't be my job. Period.

Remember: no one is paying any of us to beta test this stuff.

I'm really glad YOU found a fix, and I hope it works for others as well -- but until Apple actually puts the "good word" out there, this will continue to be a total debacle.

Oct 16, 2014 8:38 AM in response to medora66

Well I won the lottery I guess. My iPhone synced horribly (or not all all) just like everyone here 2 days ago.... I have no access to iTunes 12, future iOS releases, etc. Standard Apple software.


And when I reauthorized & reauthorized everything on my iTunes account and did fresh wipe on the iPhone 6 Plus, I have in my hands what Tim Cook has been raving about....Cheers.

Oct 16, 2014 8:37 AM in response to SOULNATIONAL ARCHIVE

Just so you know I have de authorized and re authorized both computers and my iPhone as part of the many steps to troubleshoot this issue. I've restored my phone from backup as well as set it up as a new device, multiple times. There is definitely at flaw in either iTunes or in the latest build of iOS. This was confirmed by another user who was working with apple engineers on the issue. This forum is here for users to communicate and assist other users. The old saying applies here, if you don't have something nice to say then perhaps you shouldn't say anything. Glad your stuff is working but it surely isn't THE fix or this thread would be a lot shorter. I'll continue to wait for THE fix from Apple, hopefully when 8.1 drops.

Oct 16, 2014 8:47 AM in response to medora66

The 6 Plus is great, finally a larger device that can do everything the iPhones could. Coupled with that new AppleWatch and a pair of Wireless Beats, hands down the best designed products. A good time to be alive.


Big Marc Newson fan, being a designer myself, I can finally afford some of his work. Looking forward to the Watch. I too was an initial skeptic, but the more I think about it, my iPhone will remain in much better condition, as I'm pretty hard on equipment in my line of work: http://instagram.com/jaredfrench


Cheers.

Oct 16, 2014 8:49 AM in response to th3r3ds0x

if you go back to my post where I shared what worked, I side-noted that I deleted every playlist in my iTunes library as well., But I didn't have many to begin with. That said, I noticed some weird anomalies with syncing unintended playlists, and--by accident--had deleted all my playlists during a really frustrating moment.


But I thought about my iTunes account...and devices. So I reset everything (unauthorized and reauthorized). Maybe the combination of those 2 things, but that was it, and I'm humming along. To the extent that this thread is a thing of the past to me, so I'm moving on. Thought I'd share what worked. Or maybe the Apple Gods have granted me passage. You decide....

Oct 16, 2014 9:36 AM in response to SOULNATIONAL ARCHIVE

Hello, everyone. I was the second person to post on this thread, and I haven't posted much lately, since finding my "workaround" of not letting the iPhone 6 sync to iTunes — not a permanent fix, obviously, but it has served my needs till this gets straightened out.


This morning I noticed Soulnational's posts about authorized computers and associated devices, which was greek to me. So I started digging around. On my iMac, in iTunes, I went to Store > Account > Manage Devices, and I found that the list refers to my iPhone as "iPhone (Mike's iPhone 5) associated September 19, 2014." That's the day the new iPhone 6 arrived, and I set it up through a backup. Standard procedure. In the old phone's settings, I had named it "Mike's iPhone 5," so that nickname was carried over. Now, bear with me.


Later that day, I went to connect the new phone with the Bluetooth in my car, and when the car was searching for devices to "discover," I noticed that the car was recognizing the new phone as "Mike's iPhone 5." Being a stickler for precision, I went into the phone's settings and changed the nickname to "Mike's iPhone 6." The car then discovered it by that name, made the connection, and all was well.


Till the next morning. After the phone recharged overnight and did the auto-sync to iTunes, that's when all the trouble started.


Is there perhaps a commonality here? Have others who posted here also changed the nickname of their new phone — after initially setting it up from a backup, with an old nickname? Might this be the root of the problems we're having. Note: as of right now, I have not changed ANY of my settings. I'll wait to get some feedback. Thanks.

Oct 16, 2014 12:23 PM in response to MikeinRM

Oddly enough, I recall altering the name of my fone right at the start too. Could this be the root of our ills? One can but sit back and wait. My fix is the same as yours, as in no updating. When I do come to update it in order to listen to my latest gems, I'll let u know if a miracle has happened and the tunes sync fine. Otherwise I can cane a few hours resetting it. Once a week is ok.

Oct 16, 2014 12:31 PM in response to MikeinRM

MikeinRM,


There could be a common link there. My iPhone 5 was named "<my nickname>'s iPhone". When I got a new one from AT&T, it came as "<my proper name>'s iPhone". I was immediately irritated, because the only place AT&T would have gotten my proper name would have been my credit card - I go by my shortened nickname on all my billing and accounts. So the very first thing I did was change it to "<my nickname>'s iPhone". I had the syncing issue right away, and blew it back to factory settings, where "<my proper name>'s iPhone" returned. I have not bothered changing it back, since at this point, I don't know what is or is not causing the issue. I am traveling this week and away from my home computer, so can't check to see what was authorized.


I agree with others - it is great that it worked for SOULNATION ARCHIVE, but he/she needs to understand that 1. Apple should say something one way or another, rather than allowing us to continue to be told this is a one off problem whenever we call/go to the genius bar/whatever; and 2. This thread is full of people who think they have the solution. You'll have to forgive us for not rushing to try every suggestion. Because, if you are wrong (and thus far, EVERYONE on this thread has been wrong), those of us with large libraries are in for spending an entire evening of deleting music and resyncing. I'm not wasting anymore of my time until Apple comes up with their "fix".


On the bright side, I cannot believe this thread has gone for 8 pages before a fanboi has shown up.

Oct 16, 2014 12:59 PM in response to kstaff1

that's great that kstaff1 is writing the rules for Apple's response prosedures on the boards. I barely caught this fun fact because I was immersed with a massive intact music collection on my iPhone 6 Plus.


While Kstaff1 continues to waste his/her time trying diag an old problem, I cannot believe it took 8 pages before someone had to make an insulting/bashing remark on another member who was simply offering their help & experience. Instead of hating on others because you're iPhone's inop, relax and internalize the problem, fix it and share what you discovered rather than bullying & trolling on others. Cheers, fanboi-hater.

Music Won't Sync From Itunes Correctly

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