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Revisiting iTunes/iOS sync issues

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.

Welcome to
Sync Hell

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.

If you don’t want to read everything, here’s a tl;dr version:

  • My iPhone sync issues returned, along with a huge-fake-but-limiting amount of data shown in Other.
  • There’s a known-to-Apple “very slow performance” issue in iOS/iTunes that can make some iPhones sync very slowly (fixes have been made, but not yet released).
  • A factory restore failed to complete until I rebooted the iMac.
  • After the restore, the sync worked, but I still had a huge Other category.
  • After the iOS 8.1.1 update, the huge Other category vanished.
  • I had to manually unsync/resync a number of songs to clear their gray dotted circles.
  • It may help to do a voodoo dance, sacrifice three Nokia phones, and rub your stomach while patting your head before syncing.

Read on for the gory details…except maybe for that last item, which I totally made up.

Trouble everywhere

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.”

Ugh.

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!

Final thoughts

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.

25 Comments

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  1. Hi Rob, I encountered a similar (if not identical) problem with syncing music and videos to my iPhone 6 Plus from day one with the new device. None of these problems had existed with my previous 5S. After a day of tearing my hair out and trying all kinds of steps recommended by Apple’s phone support dept., none of which were effective, I reset sync services in Terminal. That resolved it.
    https://support.apple.com/en-us/HT203202

  2. After updating to iOS 8.1.1 it at first did not seem to resolve the syncing issue. But the next morning, when I sync’ed again, all dotted circles were gone. So for now, it seems as if my issue has been resolved. But this lack of dependability is a problem I think.

  3. I am a cardio instructor in a global network of 7,000 instructors and many of us are in the same boat. Every time there is an upgrade I have issues with syncing 7,000 songs. I’m getting ready to go to work and I’m leaving on vacation tomorrow but I’m here dealing with this. I just restored and only selected a limited number of playlists/songs to sync. First, no playlists. Then I unchecked sync music, removed the music and re-synced. The playlists have now re-appeared and Im trying to slowly re-sync. The amount of resources people are putting in is crazy to solve these issues. Many of our instructors don’t apply upgrades anymore. We are definitely trying to find other options. It’s a shame because I love my iPhone 6. :(

  4. Thanks for the update, Rob. Your post almost exactly mirrors my own findings over the past two months (including huge “other” and dotted circle issues). I’m happy to hear that a fix is on its way, though I wish Apple would be more forthcoming that there was a known issue and a solution was imminent, otherwise each time I see an update with a vague description I hope that this is THE ONE that will fix the problem, only to be disappointed when it doesn’t.

  5. Very similar experience here–interesting twist. In our case, besides the 8.1.1 resolved large “other” and the duplicate song issue, we also experienced incomplete syncs due to bad disk sectors in just a couple of songs (apparently when it hit the bad sectors it quit entirely–and silently–rather than moving on to the next song). Some quality time with SeaTools flagged the bad sectors and sync is working again (new HDD on the way just in case).

  6. Ive been having very similar problems for over a year, and wasted so much of my life dealing with them. New problems arose just now as I’ve been working in manual mode- deleting songs from the iPod causes EVERYTHING to get deleted and have to resync… How are they able to release such crap software???

  7. None of the solutions on the web worked on my iPhone 6 plus IOS 8.1.2. It just would not sync with my iTunes library and the dotted circles would not go away. Deselecting the sync option did remove all the music from my iPhone but nothing got copied back when I tried syncing again.

    So I tried this and it worked – I selected the first playlist folder and sync’d. It copied all the files. Then repeat with another playlist then sync. Slow process but eventually copied all my music back to iPhone 6 plus.

    If this works for you then I suspect the problem lied in itunes getting baffled by file formats it cannot read or duplicates. When you eventually get to playlist containing such files, expect it to fail a sync. until such time, keep going.

  8. I’m right at the moment experience problems with sync.
    Add this to the fact that there is no way to transfer books without screwing the whole music you manually manage.

    This piece of software that is iTunes is a big joke, Apple definitely has become Microsoft.

  9. All I am trying to do is sync a 150 song playlist from my Mac to my new phone6. Called Apple support and they had no idea what I was talking about (dotted gray circles! how strange!). They could not find anything in the apple support docs relating to dotted gray circles so I googled it for them. oh my. My problem is also tied to trying to free up space (for music) on my phone by deleting all my photos from photo stream – only to have the photos re-sync BACK to the phone when I am trying to sync the play list (icloud is OFF!). then the ENTIRE play list with the dotted circles VANISHED from my Macbook but multiple restarts later seems to have partially appeared under a different (old playlist) name on the phone. I did do the update 8.1 in the middle of this – could a partial fix have been embedded in there?

  10. sick of crAPPLE ! Cant these stupid engineers just leave what works alone ! I recently bought and iphone 6 64GB and used itunes to first backup my iphone 4 (yes i waited a while to upgrade) and then restored the backup to my iphone 6 …now neither my songs nor videos cant be found ! WTF ..who has the time to go and troubleshoot crAPPLE bugs grrr…my time is worth more than their stupid phone software!

  11. I’m having the same dotted circles of death. I’ve spent DAYS desperately trying to sync music that has worked for years. Thanks Apple for making such awesome software!!! YAY I just spent hundreds of dollars on 64 GB that I can’t even use, awesome! And to think I was about 2 days away from dropping $2000 to switch from a PC to a macbook. Now I’m definitely not because if your “state of the art” iPhone can’t even sync simple mp3s then how can I trust your laptops? Now I’m stuck with this Apple iGarbage for the next 2 years.

  12. ive had sync issues with iphones since iphone 4, its just rubish, im alomst at the ponit of billing apple for all the hours and hours of time i have spent messing about with this rubbish phone, itunes and ios. the company i work for make us have apple crapple everything, apple crapple arnt geniuses just a company that messes about and waits for its customers to find the bugs, and then still dont fix them.

  13. same issue here with syncing to phone either fails or whatnot apple said it was my computer being unable to transfer large amounts of data via usb but thats pretty fake considering I tried later using my portable drive and I transferred 30 gigs to it no problem; I fixed the problem for awhile by uninstalling all of apples related services like bonjour and the other crap and that worked for awhile but its back yet again.

  14. Here is what I did after 3 days of dealing with this other data, I am jail broken iPhone 6 (8.1) I went to Ifile downloaded from Cydia, went to iTunes Control under var/mobile/media and deleted every freaking thing, all the artwork, every folder in there and rebooted. After that there was no music on my phone and I was asked to restore of set up as a new phone. I did some cleanup work with iTunes first before re syncing and when I plugged the phone back up to iTunes all my other space 32 go was gone! Now it’s down to 2.92gb with 19gb of music and I’m so happy I kept my jailbreak! So try using ifiles or there is another program to get to your phones root directory from the computer I forget the name but it’s free. I hope this helps
    Chi town RN

  15. My wife has been complaining for some time that songs kept disappearing from her iPhone, which I took with a pinch of salt because I could sometimes find them (cough) but she was right: all our devices seem to be massively messed up thanks to syncing issues.

    My iPod Touch (iOS 8.1.3) was hanging on sync, so I tried the restore thing and it seemed to work, but then it continued to fail to sync. I tried your two tips today of deleting duplicates and deleting the iPhoto cache, plus the usual rebooting/turning off and turning on again trick and managed to get some appearance of syncing (on wi-fi, no less!), but when I looked in iTunes I saw loads of tracks grayed out, despite the sync having “completed” for the first time in three weeks. It can’t be something in the albums themselves since you’d get half the tracks from an album, or none at all, or all.

    The thing is: I wonder how many people are walking around with iTunes libraries that are simply not fit for purpose, yet they think it’s something that they are doing wrong.

  16. What appeared to work for me (and it may only be a very temporary fix) is this:

    I turned off Sync Music, accepted that this would remove the music from the device, and then pressed “Apply”. Then (possibly important) I restarted the device, went into iTunes on the device and manually deleted the purchased songs which are left on there when everything else is removed. Then I restarted again (for luck) and turned on Sync Music again. Rather than let it try to add everything, I instead selectively sync’d fewer music files, and that seemed to work well.

  17. Apple have morphed into Microsoft. They refuse to acknowledge that they have screwed up the use of their flagship , iconic product – iTunes. They have reduced it to the level of the 80’s diamond rio. Every employee involved ? You suck at your job.

  18. I just encountered the same issue with my 6 plus. I tired creating playlist and it still did not work. I removed duplicates then erased the music on the device. Then synced my music back and magically the 100 songs that were ripped from CDs finally installed to my phone. Thank you so much for sharing your story

  19. Count me in as another one who’s had this issue – it seemed to have cleared up until like a dumbass I decided (for what reason I now can’t remember), that I needed to rebuild my library, and that I didn’t keep a backup of the .itl file that was actually working with syncing. The next 12 hours were filled with me doing restores from the cloud, resets, and every damn thing else trying to get my iPhone back to a state where it would sync all music, instead of pulling up a result with half of the tracks marked by that dotted line circle. Manually dragging, downloading from the cloud, deleting the original file in my library and adding again from the cloud – nothing would work. At the end of the day, what I think solved my problem was something similar to what E Fryer mentioned above – using a third party tool (in my case Explorer, which doesn’t require jailbreaking) to go into the iPhone’s Media folder and delete almost everything – album art, photos, preference lists, everything.

    I’m not actually going to recommend doing it, because at that level of folder interaction I think you could be pretty close to bricking your phone, especially if, like me, you had no idea what half of the files were, if they were generated by me or if they were critical system files (after 12 hours I was angry enough not to be rational and lucky enough to not only escape without injury, but in fact solve my problems!) What I think is fairly clear, though, is that iOS and iTunes can leave a huge amount of rubbish data in the phone’s memory, even when you do a full delete and restore. And if there’s some piece of left over data like an cached album art from a file, iTunes is going to think that some other process is managing the transfer of that data. Worse still, it looks like other iPhone apps like Photos can have an impact on what I would consider to be a totally unrelated app like Music.

  20. I’ve had this problem for a couple of years – my 64 GB iPhone 4S takes ~2 hours to sync. Sure enough, I went and looked for the grey dotted circles and I’ve found them but not on songs that were ever downloaded from iTunes. Similarly, doing a factory restore and syncing ~10K songs converted from MP3 to AAC back to my computer takes about 2-3 days, most of the time spent in Step 7 of 7: Waiting for items to Copy. (For reference, the conversion process of the MP3’s to AAC when copying them to an iOS device is about 1000 songs an hour, so conceivably my phone should really only take about 10 or 11 hours to sync, all things considered.)

  21. Similar problem solved! iPhone 6 running 9.0.2 and iTunes 12.1.3 Dotted Circles

    I had a similar problem with about a thousand out of four thousand songs not transferred and left with dotted circles on the iTunes song lists. The sync process executed, but just stopped before transferring all the songs and finished seemingly normally with no error report. Further sync attempts went through the motions with no abnormal report but did not transfer any more songs.

    After reviewing a variety of posts, I focused on purchased songs. I had several in the library and on playlists marked for transfer for which my phone is no longer authorized. After deleting all of those from the library, I reran the sync. The remainder of the songs transferred and the dotted circles in iTunes were removed.

  22. Found a fix. Let’s call it the AIRPLANE MODE TRIPLE SYNC ZERO method.

    1) put in airplane mode.
    2) sync with zero songs selected under iTunes in you device music page. Actual sync with zero songs.
    3). Sync by unchecking music page in your iPhone section of iTunes. So now you are just doing a sync with no music to reset the music section internal to iPhone.

    You should now have a blank music section in your iPhone. The next sync will put all your songs on the iPhone regardless of duplicates. Am using iTunes 12 on windows 10. and iOS 10 on iPhone 5. This will work every time to load music. No errors in sync.

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