iTunes syncing is broken: Apple, please fix it

“I remember the days when I’d get a new CD, rip it to my iTunes library, connect my click-wheel iPod, and have the music sync in less than a minute,” Kirk McElhearn writes for Macworld. “Ah, the good old days were so much better…”

“Now, syncing an iOS device — iPhone, iPad, or iPod — is too often an ordeal. And it is because it’s become untrustworthy,” McElhearn writes. “Will the sync work at all or will your content disappear and be transformed into something that fills the amorphous “Other” category in iTunes’ capacity bar. Will all of your content sync or just your music, or music, or apps?”

“In its current state, iTunes syncing is broken and it can only be fixed by Apple,” McElhearn writes. “Here are some of the most common sync problems, and, in some cases, solutions or workarounds to get media files onto your iOS device.”

Read more in the full article here.

53 Comments

  1. I read this article early this morning. Personally, I haven’t had any of the problems he describes except the mysterious “other” data that eats up some of my space. I use iTunes Match to get music onto my iPhone and iPad, but I plug in to sync movies, audio books, or any other content that would take a long time to load over my wifi network. I guess I’m using a hybrid of cloud and physical connections.

    1. The “other” pops up for me if I try to autocompress Apple Lossless to iTunes plus. The only way I can avoid the problem is to convert files to iTunes plus within iTunes and then copy to my phone.

      Trying to convert a large number of audio files while syncing to the iPhone effectively bricks the phone; the only way out is to restore to factory settings and start over. No fun at all. Apple really needs to figure out that some people have large collections of lossless audio.

    2. Consider yourself very fortunate. Many of us avoid music match because we have cellular data plans to worry about. By the way, you are expanded other is probably do to streamed music getting stuck there.

      ITunes has been screwed up for years! It got really bad when iOS 7 came out and I had to restore my phone about every three weeks just to control the expansion of “other” and to stop songs from vanishing.

      Since iTunes 12 and iOS 8 syncing audiobooks has become a hit or miss operation, sometimes requiring up to four separate attempts.

      Sometimes when I try to stream video to the phone the video gets stuck in “other” the only way to remove it is by wiping the phone and restoring from a good backup.

      ITunes never gets updates it only gets facelifts. Apparently the programmers feel that if we’re sufficiently confused by the new interface we won’t notice that all the old bugs are still there.

      Obviously complaining here won’t do a bit of good, we have to send all our complaints directly to Apple using apple.com/feedback.

      1. Sounds like you’ve been going through a lot of bull crap for years. Honestly, I don’t have the problems you describe and never have. As for iTunes Match, I’m on a 4GB data plan that is shared with another user on my account. I’m usually within range of a wifi connection, so I don’t use much data. iTunes Match doesn’t seem to consume a lot anyway. When I signed up for it, I took note of the increase in cellular data usage. It was negligible.

        1. It hasn’t been fun, but some of the comments I get from Applecare have mitigated the pain a bit. One problem I had consisted of the iCloud icon showing up next to music videos even though they were loaded onto the phone. I spoke to a senior adviser at Apple who outright didn’t believe me. I put my phone into airplane mode, went to the videos app Took a screen shot and sent it to him. There was the airplane icon in the upper left-hand corner and a bunch of videos with cloud icons to their right, which is impossible.

          His comment very likely didn’t conform to Apple’s tech support guidelines! 🙂 He emailed the screen shot to the engineering department and that bug was squashed in the next update.

    3. I’ve had the problem described: I’ve had songs I’ve purchased on the iTunes store disappear from my iPhone. I can redownload them, or resynch, but if I’m in an area without internet access, I’m screwed. Apple needs to fix this problem!

  2. Something corrupted my iTunes the other day and I’ve ended up with songs having been relabelled, pictures added as tracks from iTunes extras content, tv shows showing up as music tracks with labels from albums. Complete pain. You’d that such an important part of Apple’s business would be the most robust thing they do.

  3. Perhaps it’s like the problems with iPhoto. Eventually, I had to break up my photos into smaller libraries because the database could not manage properly. Now I keep my photos in libraries by year.
    The iTunes dabs may be reaching its practical limits if you have a huge number of items in it.

    1. There are a ton of things broken in iTunes. I could write a large book on some of the things that are broken and how to fix them. Here are a few, summarized (search online for details, or ask if you can’t find them).

      Starting with your iPhoto problem:
      Sync freezes or crashes on photos:
      Try deleting the iPod Photo Cache on your Mac, and allowing it to rebuild.

      Sync only works via WiFi:
      Try swapping out your USB cable or even plugging it in to another USB port, directly on your computer.

      Sync fails on music
      Check library for duplicate purchased items or duplicate iCloud errors.

      Falsely out of capacity
      Remove items, resync, and then add them back. Try removing a very large game or other app. The problem here is that iTunes doesn’t delete and then add. It adds, and then deletes. If you’re doing a large sync of large apps, it may go over capacity due to having both the new and old version of the app.

      Won’t sync over WiFi or USB
      Restart iOS device. Restart Mac.

      Won’t sync reliably over WiFi despite strong/stable connectivity
      Welcome to the club.

      “Other” size is insane
      This can happen when a sync has failed. Try rebooting the device and following the above to restore a successful sync.

      “Other” size is extremely large despite successful sync
      This one could be an entire book in of itself, but the things to try (in order) would be:
      1) Check for data files in apps. For example, if you have a 3rd party movie app and that app has a bunch of large video files, that’s going to show up as Other.
      2) Check for Software Update file, if present delete or update.
      3) Sync without music, photos, or apps selected removing these, and then select these to sync again (adding them back)
      4) If you’re jailbroken, run iCleaner.
      5) Restore from Backup.
      6) Delete old texts, especially those with media. If you’re jailbroken, there’s a better way to do this.
      7) if you’re jailbroken, search for corrupt media databases. If a sync fails, it can corrupt a database, but instead of over-writing it when it restores a new database, it can still be present on your device. You can search for this, remove it, and then resync. This has happened with me with both photos and music.
      8) If you’re jailbroken, use the terminal or ssh to find large files. Search for files over say 100mb and look for things that don’t make sense.
      9) Go nuclear… Restore as New. Full Restore.

  4. So true!!!! My iPhone 6 plus is giving me hell…. Syncing to my iTunes library. Also getting a 49Gb “other” occupying space on my phone…. I’ve being at the Genius Bar and on the phone with costumer service at Apple. And they haven’t been able to help me. I just keep resetting my phone as new and the same thing happen again. Only the song that I have bought from iTunes load up. Help Please!!!!

    1. To remove the large amount of “other” check and uncheck
      Sync automatically in iTunes preferences. The wiping and recovering from backup will also work but is exhaustive and I’m always afraid my contacts and info will be lost. Hope that helps until Apple gets someone to fix the tentacles in iTunes

  5. I have had all of these problems–with my iPhone 5 and my new 6+. My wife will not connect to iTunes under any circumstance for her 5S. Best to use one of the after-market programs for transfers, and don’t ever trust iTunes to do this.

  6. Of course my experience is anecdotal, but there is a lot of truth to this article from what I have seen. JUST YESTERDAY, iTunes sync got all confused and hosed up my iPhone 6. The “other” category kept saying it was some ridiculous size of about 47 GB, and whatever I tried wouldn’t clear it until I reset my iPhone back to factory conditions. What a hassle….

    I agree, iTunes sync is a crapshoot whether via wifi or tethered.

  7. Yes, I have found it impossible to sync my iPhone 5 or my new iPhone 6 Plus. Same thing for my wife–she has not synced for years to iTunes–just to 3rd-party programs. That’s definitely the best way to go. It still leaves me the task of building playlists directly on the phone, but how is it that all of these 3rd-party programs are able to accomplish this yet Apple can not?

  8. My iTunes got confused last night.. Couldn’t sync my iPhone 6 at all..
    Even plugged into my iMac it couldn’t find it.. Yet iexplorer and phoneview could.
    Restarted iTunes..
    Restarted iPhone..
    Didn’t work.

    Restarted iMac plugged iPhone back in, asked if I wanted to trust the computer… Still shows my iPad at 100% and connected, yet I know it isn’t and last night it was at 28% when I put it down.

    Most of the time iTunes works just fine, but the days it doesn’t…

  9. My iTunes is OK but it seems like Apple software quality in general is getting worse. Have you ever the latest iMovie? How about ios 8.0 or OSX 10.10.0? It seems to be getting worse not better. My new rule is wait for the first update to a new release before even considering installing. Steve is probably rolling over in his grave as Apple software quality trends closer to that of windows.

    1. The perception (and fact) of “Software getting worse” is a direct correlation to the increased complexity that must be managed by that software. 10 years ago, iTunes had 2 or 3 devices to know about. Now it has dozens upon dozens. That’s gotta be a tricky process to manage effectively.

      1. You and I have not experienced the frustration that the other people on this forum are posting about. That frustration must be particularly bad when you are dealing with Apple products which are just supposed to work.

        But I would like to know more about these problems – the percentage of users who are encountering these bugs. There are likely some factors or combination of factors which these people have in common.

  10. iTunes is a mess these days.

    It’s as if the designers know exactly how all the buttons and dials work, so they went ahead and designed something for them.

    For example, I’ve reduced by half the number of podcasts I subscribe to, simply because of the sync problem. Do I still listen to that missing half? Sure. I download them to my desktop and listen from there.

    As for the “OTHER” problem, it’s still there. Not with my 64 gb 5G Touch. But the Other category eats up my 16 gb iPad Mini.

    Apple, sad to say, would rather blaze bold new trails into the future than fix the problems of today…and yesterday.

  11. I wish I knew what was going on here. I’ve rarely had any problems with sync and, when I did, it was because I did something stupid. I’ve learned from each one of those and it’s really solid now.

    I have a friend that always does “absolutely nothing wrong” and have issues like the ones described here. I want to help, but it seems like solving the same problems over and over again. I ask “What’d you do so that we figure out how to not have this happen again.” They don’t like to hear me use the same exact phrasing they’ve used over and over on tech calls 🙂

    1. What can you do wrong? You tell iTunes what to do and it either does it or it doesn’t. If it does it then it’s working, if not, it’s broken.

      If I tell iTunes to sync x audiobooks and remove y audiobooks and that isn’t the result of the sync, then iTunes is broken.

      I find it very annoying when the few who don’t have problems automatically assume all is perfect at Apple and the people having problems are doing something wrong.

      iTunes has been screwed up for years and needs more attention than an interface change every so often. Apple needs put some great programmers on both iTunes and iOS in order to get the two working together properly.

      It really sucks to try and sync a few things to an iDevice and worry that the sync will fail and cost many hours of time to do a complete restore, and even they occasionally fail. I started a restore one night after restarting both the computer and iPhone and woke up with no media on the phone. It was actually there but all of it got loaded into “other” memory.

      It’s a bug-ridden piece of software and Apple is doing nothing to fix it. Stupid, because it’s the one piece of software that might convince Windows users to consider trying a Mac, and if the Windows version is as buggy as the Mac version, that won’t happen.

  12. Totally agree! To get my entire music library to sync requires me to make selections in the sync preferences that make no sense. Getting movies to sync is another nightmare… Apple, please fix this!

    1. What works best for me is to sync playlists manually! What doesn’t work is the white background my eyeballs hurt! Jesus Mary Joseph is it to much to ask for the option light or dark background! I still have 10.7 on another computer and it is a better experience with cover flow and dark background!

      1. Funny, I was syncing all my music over and decided to change to playlists. After the sync all my music was still there, but only three playlists had synced. The Genius playlist and two playlists I had Unchecked! After a while on the phone with Apple tech support trying lots of things that didn’t work, I gave up, wiped my phone back to factory specs, grabbed a good backup from a backup drive and did a complete restore. The following sync cooperated.

        Restores shouldn’t be part of regular maintenance but unfortunately have been since iOS 7.

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