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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

Jan 6, 2015 11:32 AM in response to matt4692

So I've had this same problem and haven't been able to get it to work. Reading through here gave me a few ideas, so I poked around in iTunes to see what I could do.


First, I unchecked sync over wifi.


Second, I went to File>Library>Organize Library and checked the first option (only one highlighted for me) Consolidate Files. This takes all the files spread around your computer and puts them into one single iTunes Media folder.


Last, I clicked sync, with Selected Playlists, artists, albums, and genres selected.


What I saw was a complete departure from what previously happened, it physically copied an additional 1491 songs onto my iPhone, so now my iPhone library is back up to 3898 songs vs the 2407 it's been stuck at since I got it.


I just did this as I typed, and am now a happy camper. i hope this helps someone else out there, this was definitely very frustrating!


P.S.


Now I have the unenviable task of migrating my iTunes from my Windows PC to my new iMac. Wish me luck 🙂

Jan 22, 2015 4:50 PM in response to Thejinxed1

Just got my phone last week. Was able to sync all music I wanted to the first time. After a few days decided I needed to sync some more and was not able to sync anymore. The fix I just found that worked was to go to the album, right click, add to playlist. My phone was listed and iTunes was able to send the album. Hope this helps.

Jan 22, 2015 6:36 PM in response to Thejinxed1

Jinxed,


It keeps everything organized with a folder per artist, a folder inside of that per album, all under a main iTunes folder. So the folders would be setup like this: iTunes>Artist>Album>song files


Sorry it took so long to reply, I had remember to come here when I got on a desktop. I kept trying from my iPhone in Safari and it wouldn't open the reply dialog, and in Opera for iPhone, it'd open the dialog but freeze when I started typing. Of all the websites that you would think supported iPhones... I was about to notify support

Mar 3, 2015 10:54 PM in response to matt4692

FIXED MY SYNC PROBLEM:


Finally found out why all of my music wasn’t syncing….. After the short sync time, a box would come up stating that there were “errors” when syncing. They were 14 tracks that had been deleted, but were still somewhere in a playlist.


If your getting a sync error message at the end, and there was a problem with some tracks.

  • Take a screen shot of the “error” list.
  • Go to your Library, click on Music, then Playlists.
  • Search for and delete each individual track name from the "error" list.
  • Click on iPod and “Sync” again.


Pretty silly that it wouldn't just skip those tracks and sync the rest. Hope this helps.

Mar 3, 2015 10:59 PM in response to matt4692

FIXED MY SYNC PROBLEM:


Finally found out why all of my music wasn’t syncing….. After the short sync time, a box would come up stating that there were “errors” when syncing. They were 14 tracks that had been deleted, but were still somewhere in a playlist.


If your getting a sync error message at the end, and there was a problem with some tracks.

  • Take a screen shot of the “error” list.
  • Go to your Library, click on Music, then Playlists.
  • Search for and delete each individual track name from the "error" list.
  • Click on iPod and “Sync” again.


Pretty silly that it wouldn't just skip those tracks and sync the rest. Hope this helps.

Mar 25, 2015 11:13 AM in response to matt4692

How to transfer your data from iPhone 5 to your new iPhone 6 Plus with iTunes (windows 8)


1. Backup your iphone via a cable to your computer (you must locate all your

2. Turn Sync over wifi off

3. Go through all the setup screens on the iPhone, insert sim, sign in to itunes

4. Restore from iTunes backup, connect device to your computer via usb cable

5. Perform restore, cancel any update messages or warnings

6. Now after this has completed, all your previous iPhone settings & data will appear on your new iPhone 6

7. If your a business customer check your Exchange email account is connected & working (will require your passwords)

8. In iTunes select the phone

9. Summery, disable sync over wifi

10. Enable aeroplane mode on your new iPhone

11. While it is still connected to your pc, make sure you have all your items enabled for sync

12. Music sync entire library (ignore the warning about erase data on the phone)

13. Pictures sync

14. Apps sync

15. When you hit apply all your data will be migrated, to check this disconnect the phone from the pc, disable aeroplane mode.

Go to Settings > General > Usage > Manage Storage (and all your apps and sizes will be displayed)


Thank you

Music Won't Sync From Itunes Correctly

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