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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

Jul 22, 2015 9:35 AM in response to matt4692

I just experienced a weird music syncing problem as well (iPhone 6, iOS 8.4, iTunes 12.2.1.16, Windows 7). My issue was that certain songs in my library would not sync to my phone. For example, I had 10 songs in a playlist and several of them would never sync, regardless of which playlist I added those songs to.


The solution was easy for me.


1. In iTunes, uncheck the "Sync Music" checkbox for your device. This will remove all music from your device.

2. Do a hard reboot on your device (Hold Power button and Home button until the device reboots)

3. After your device reboots, make sure it's connected to your computer again.

4. In iTunes, check "Sync Music" and check the playlists and music you want transferred to your device again.

5. The songs that weren't syncing will now sync correctly.

Oct 24, 2015 11:36 PM in response to matt4692

Wow, those are a lot of steps to get your entire library to sync with your Iphone. Who would've thought that it would of been so difficult to in this day and age. I'm getting lazy with keeping up on all these ap updates. When I was a kid, we used to make fun of people who worked on PC's, it seems like the tide is turning.

Music Won't Sync From Itunes Correctly

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