Music Won't Sync From Itunes Correctly

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.

Hello Matt,

I too had the exact same problem and I believe that I have found a solution.

Prior to connecting my IPhone 6 to my MacBook Air I turned off the Wi-Fi and also placed the phone into Airplane mode. I then connected my phone, checked the music I wanted to download then hit sync. It seems to have loaded all my songs this time.

Hope this helps you and others.

Matt, how do you "wipe the songs from the memory" (of the iPhone, I presume)? I've tried so many fixes, I'm losing track of what I've done. The suggestion above from sgblakley didn't work for me either.

Having similar issues with my 4s and IOS 8. iTunes will only sync the 56 songs I have purchased from the iTunes store and nothing else. It goes through the sync steps, gets to tracks, says it will sync, shows the amount of data it will take, thinks for a few seconds then stops completely, reverting back to having 10GB free and no songs waiting to sync. I have performed full and partial restores on the phone, stripped all music and started over, tried airplane mode, etc, but nothing wants to make my music sync.

I bought the iPhone 6 (128GB) to sync the 79GB worth of music, but have ran into this problem as well. In a different thread I read the AppleCare solution, when another iPhone owner spoke to them on the phone, was that the libraries where too large to upload to the phone in ones sitting. I find that a little silly, but I am giving that a go right now, uploading it in smaller chunks. However, before doing so, I did reset my iPhone to factory setting and did not restore it from a back up. The other things I did is made sure the new iPhone was tied to my iTune account. That can be checked under account / manage devices with in the iTunes store. And yet the third step I took, only because I read it on a different thread, was not check sync this iPhone over wi fi. Willing to try anything to see if it works. Keep you updated.

So here is the final steps I took to finally get the 79.15GB (15,389 songs) that is my music library to sink.

1. I had to restore phone to factory setting after multiple attempts to sync my music library only to think it was complete, but find 40GB of something under the category of "other".
2. I did not restore my iPhone from a back up, I did it as a new phone.
3. Once I finished restoring and before I plugged it in to sync, I downloaded all the apps I use to the phone itself from the app store. So my plan was not to sync apps via iTunes on my iMac. I only was going to sync music and movies and that is only because I has a ton of CDs converted to MP3s before I started buying everything through iTunes.
4. Since I have a large library typically I check covert songs to 128kbps AAC, however this time around I did not do that.
5. Once I plugged in the iPhone for the first time to my iMac, using the cable provided with the iPhone, I told iTunes to only sync music and movies. I checked all the playlist and movies I wanted on the phone. I did not do entire library. Also, my intent was to check everything I wanted to do it one big swoop and not return for second.
6. I then hit sync and it worked.

A few things to note. I never interrupted the sync. I allowed for the iMac to think however it long it needed in what ever step it was. I didn't get inpatient this time around. I also did not check sync via WiFi (which I regret). I regret this because now I don't intend to plug into the iMac for fear that it will put some content back under the category of "other" as it has in the past. Restoring and uploading and do it again has been a 3 day process that I don't wan to do again. I intend to use the phone like it had no home base and only download straight to the phone from the music / app store. Anything I purchase on my computer or phone will be available via the cloud to download onto my other devices. This is where I stand now, the hope is that the next iOS or iTunes update will fix whatever error is creating all this loop jumping.

Same problem. iTunes Match turned out to be the culprit.

Solution:

Also turn off iTunes Match in iTunes on your computer.

Then resync with "sync music" unchecked.

Lastly, sync again with music checked.

After reading KrispE's comments, I checked my iTunes match and it was not turned on, but Genius was on right next to it. I shut off Genius and everything else started to synced up flawlessly. I turned Genius back on and it went back into the same behaviors of not syncing music properly. Leaving Genius turned off until Apple figures themselves out on this one.

Bumping this up, to see if anyone has found a long term fix. Everything here works, but just once. Next time I sync, the red circle comes back. I've been a loyal iPhone user since the first phone came out, and this is the final straw for me. I've wasted every evening since getting the new iPhone resetting to factory defaults, trying things, thinking I finally have a fix, syncing up 7000+ songs, installing and configuring all my apps, and getting my phone to a usable state, only to sync the next morning and 2/3 music randomly blown away.

I have never signed up for iTunes match. If this is an evil attempt by Apple to push me towards their streaming service, I'll sell my iPhone 6 and switch to Android.

I am in the same boat. My fixes are one time only fixes. There is no going back to the iMac to sync again if I don't want to restore to factory setting. Just a quick question: have you found that plugging in your phone with the Apple provided cable vs. one you already owned helps? I now have had to write the exact steps I take to make sure I get the one time sync right. However one of those has become using the provided Apple USB cable.

iPhone 6 - 128GB

I only have the apple provided cables, so I don't think that's it.

Same exact situation for me. I'm not sure if it occurred only when I switched to "Sync entire music library" or if the problem would have occurred anyway. I turned of iTunes Match on the Mac before syncing. I then did a full restore of the phone and loaded apps one by one. Sync'd the entire music library, and I watched the entire process. Everything seemed fine. Went out, started streaming to bluetooth in my car, and bang--most of my songs are gone.

I'm having the same problem. Certain tracks just won't sync. The status bar says "Waiting for items to copy."