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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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.

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Music Won't Sync From Itunes Correctly

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