After getting my iPhone 6 in early October, I was initially excited by all the cool tech in my new phone. Until I tried to sync it, that is. I eventually got so frustrated that I emailed Tim Cook for help. From that email, I wound up talking to Apple's engineers, who eventually solved my sync issues—it turns out they were related to duplicates of long-ago-purchased songs.
And for a while, things were great in iPhone 6 land. Then I ripped a few new CDs, and noticed that they didn't show up on the phone. Uh oh. Even worse, when I looked at my iPhone in iTunes, the Music section contained hundreds, if not thousands, of the dreaded gray dotted circles.
This seemingly innocent symbol means that the indicated song did not sync—the information about the song made the journey to the phone, but the song itself did not. Argh! Read on to see how I muddled through this issue, with some advice that may, or may not, help you with your own sync issues.
Read on for the gory details…except maybe for that last item, which I totally made up.
My latest sync issue became apparent when I connected the phone a week or so ago. The sync looked like it was normal, but then got stuck at "Syncing Music to iPhone (Step 7 of 7), waiting for items to copy." I left it there for an hour, and nothing budged.
I also noticed that I had the devlish "mega Other" issue:
That Other block represents about 45GB of data—none of which is really used. The iPhone and iTunes, though, both think it's gone. Restarting my Mac and iPhone didn't fix the problem at all; it was seemingly permanent, and iTunes treated the space as gone.
To solve the sync and mega-Other issues, I first tried removing iPhoto's iOS device cache; my buddy Kirk McElhearn suggested this one, and it seemed to work…almost. In Finder, navigate to your iPhoto Library (quit iPhoto first), right-click on it and choose Show Package Contents. In the folder that opens, find and delete the folder named iPod Photo Cache. Then sync again.
When I did this, my phone synced over 3,500 photos that I didn't even know I was missing! Unfortunately, it then again got stuck on the last step, and didn't copy any music.
At this point, I punted and emailed my contact at Apple from the last go-round, explaining that the non-sync had returned, and that it wasn't related to duplicates (as I'd confirmed with Dupin that I didn't have any duplicates).
Syncing slowly into hell
My contact had me install some logging tools, and eventually wrote back with interesting, albeit not really usable, information: My iPhone had triggered a "reset sync" with iTunes, and I then hit a bug in iTunes/iOS that led to incredibly slow sync performance. (I was told that they've fixed the issue in both iTunes and iOS, but those fixes are not yet released.)
He suggested I leave the phone plugged in and "stuck" at the final step for as long as possible. I plugged it in one evening, went to bed, and checked in the morning. Amazingly, it appeared to be copying music—the status line indicated "4 of 573" or somesuch. Item four happened to be a 90MB music video, so I let it sit there a while. But the progress bar was stuck; after two hours, before-and-after screenshots proved it hadn't moved at all.
I know I was told it was slow, but if that was really the rate, there's no way I'd have time to let the iPhone finish syncing all 4,500 songs. So I pulled the plug, and reconnected. This time, it got to syncing music relatively rapidly, but locked up again while syncing a song. I let it sit for an hour, only to be greeted by an error message:
The iPhone "iPhonetastic" cannot be synced. The device timed out."
The nuclear option
At this point, I decided to start over, and chose to do a full factory restore. That, too, ended badly:
The iPhone "iPhonetastic" could not be restored. An unknown error occurred (2006).
At this point, my iPhone was useless, displaying the "connect to iTunes" image. But connecting led to the above error message. Not good.
Thankfully, a reboot of the iMac magically solved the problem, and the restore proceeded. It didn't, however, actually do a factory restore, because when it was done, all my apps were already installed without my having to restore from a backup. So I'm not sure what happened, but I had my phone back.
Magically, when the restore was done, music started syncing! It made it through all the songs, and I thought I was free and clear. But I still had the "mega Other" problem, and my Apple contact didn't have a fix other than "another restore should clear it."
As I was just about to start my second restore, iOS 8.1.1 came out; after installing the update, my iPhone's Other bucket was back down to its usual small self. Hooray!
The last step
I thought I was done—my music had synced, so I was set. But a glance at the Music category on the iPhone showed that I still had about 150ish gray dotted circles. Oddly, these songs were actually on the iPhone—they'd play fine when the phone wasn't connected to the computer (and I don't use iTunes Match).
To get rid of these ghostly gray dotted circles, I created a playlist (in iTunes, not on the phone) containing all of the troublesome songs. I then unchecked all the songs, and synced the phone (my phone is set to sync only checked items).
After confirming that this removed the songs from the phone, I went back into the playlist and checked all the songs. When I synced again, the songs were added back, and all of the gray dotted circles were gone. Hallelujah!
As Kirk observed earlier, there are some definite problems with iTunes and iOS sync. I don't think these issues are hitting most users, or even a majority of users. But with tens of millions of new iPhones out there (plus the millions more in the existing base), even a tiny percentage of users with issues is going to generate a lot of feedback.
If you're still stuck in sync hell, try a factory restore (painful, I know), followed by some manual music management to remove any lingering gray dotted circles. No promises, but it worked for me…for now, at least.