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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

Nov 4, 2014 4:52 AM in response to matt4692

I'm actually surprised that Apple has not addressed the issue as this is clearly a bug in iTunes. If you open console on your Mac and view the error messages generated by iTunes you may find an entry iTunes[384]: BUG in libdispatch client: kevent[EVFILT_WRITE] delete: "No such file or directory" - 0x2 which may or may not be the culprit. You may also find other errors such as iTunes[384]: tid:1494b - unable to query device capabilities, or iTunes[384]: clip: empty path. Error messages aside, the best work around is to remove all music on your iPhone (Settings>General>Usage>Manage Storage>Music and delete all music) while the phone is in Airplane mode, then reconnect to iTunes and manually select the songs/playlists you want to sync. DO NOT HIT THE SYNC BUTTON - only hit APPLY, and your music should sync.

Nov 12, 2014 2:57 PM in response to matt4692

Good news and bad news after a couple of weeks of everything working fine.


The bad news: After adding 7 songs from a non-iTunes source, my syncs are going crazy again, taking forever to complete, and most of my album art is gone.


The good news: The songs are still there.


Time to remove all 9,500 songs and start over again.

Nov 16, 2014 10:07 AM in response to matt4692

HI


still experiencing the same problem.


iphone 6. 128gb. usb (Apple) into pc.


Unless I do a factory reset of iphone and sync from new I cannot add additional albums / songs. I have uninstalled and reinstalled iTunes. I have left iTunes to sync forever.


I Have contacted Apple support by phone (no good ). I have tried to get an appointment at my local apple store but when I identify that it's a syncing issue on my iphone the process reverts my to phone support.


iin iTunes I can see the added folder under my iphone icon but it does not sync to my iPhone.


I've looked through numerous threads but there does not seem to be a conclusive answer. Is it my human error or is there a genuine issue with the software / phone ?


MAny any thanks to all in advance.

Nov 16, 2014 11:31 AM in response to Nev Swift

I'm no expert so take this advice with a grain of salt, but here's what I'd do:


Uncheck "music" in iTunes, which will tell iTunes to wipe all the music from your phone

Sync


If the music is still there on your phone, remove it from the phone via Settings / General / Usage / Manage Storage / Music / All Songs / Swipe Left / Delete

This last step often doesn't work on the first try; last time I did it it took 3-4 tries to work. While deleting your phone will act like it's locked up; just let it finish.


Then connect your phone again and attempt to resync your music.


Good luck!

Nov 25, 2014 8:53 AM in response to Nev Swift

I had waited to upgrade my 6 devices until I bought an iPad Air 2 and an iPhone 6 Plus this month. I immediately began having the music sync issue on my devices. It took me a couple of days, but I finally got the music to sync. I started out assuming it was a problem with iOS. This morning, I decided it might be a problem with the latest version of iTunes, so I changed my approach.

Here is what I did: (Windows 7 Ultimate)

1. Copied my entire iTunes Music folder to a backup folder.

2. Opened iTunes and selected all of my music, then deleted it.

3. Copied my entire music collection from the backup folder into the iTunes Music folder.

4. Added the iTunes Music folder to my library in iTunes.


My music synced perfectly after doing this.

I hope this helps others.

-Bill

Dec 5, 2014 12:37 AM in response to matt4692

I am having the same issue with my iPhone 6 that i purchased about three weeks ago and it is a REALLY irritating problem i think its the iOS version because now my iPad is having the same issues with syncing new music since i updated it and they really need to get it fixed because i did not buy 128gigs for my health i wanted it so i can have all my music on my phone

Dec 6, 2014 9:25 PM in response to applelover1991

I fought with this issue for days and tried many suggestions in this discussion. The suggestion to delete duplicate songs seemed to work for me and my music is now synced to the iPhone.


Select Music > View > Show Duplicate Items > delete ALL of those songs > go to the Recycle Bin and select the music you just deleted (minus true duplicates)...you can sort by 'Date Deleted' > Click the Restore the Selected Items box under the menu (songs should not show up as duplicates any longer in iTunes) > Sync device in iTunes


note: I did not ever reset the iPhone


I hope this helps someone and thanks to those who tried to help all of us!

Dec 23, 2014 6:49 PM in response to matt4692

I am not sure if this solution has been posted already, or will be helpful to anyone, but I worked for me.

I have also had the same problem that people have been describing. I’m using an iPhone 6 and iTunes 12.0.1.

I noticed that new albums I was adding to my iPhone to sync were not. They appeared grey in the ‘music’ section of my iPhone when it was plugged into iTunes.

I tried to uncheck music sync and ended up with 35 gb (about the size of my music) as ‘other’ and an inability to sync any music at all as it was now over my device limit.

I followed these instructions: http://forums.macrumors.com/showthread.php?t=1786762&highlight=syncing+issues on the advice from another forum and tried to resync. This post by Geekdad seems about the same solution https://discussions.apple.com/thread/3909940

Even then it hang for ages with “waiting for changes to apply”. After about 2 hours, I checked “sync only checked songs and videos” in summary, pressed apply, and it started working!

The next sync only hang at “waiting for changes to apply" for 40 seconds or so. All good so far with future updates!

Dec 30, 2014 8:11 PM in response to matt4692

After trying A LOT of the fixes posted I ended up figuring it out on my own. Itunes library couldnt find my music and that was because I moved it all over to my external hard drive. I erased my itunes library and it asked me if i wanted to scan for music... so I did..... and it found and synced all my recent music that I hadnt moved over yet!!! So I now have songs on my phone!!

Music Won't Sync From Itunes Correctly

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