How I Would Fix iTunes, Part 6: Fix Syncing

(This is one of a series of articles looking at elements of iTunes that I think need fixing. I’ll choose one element for each article, and offer a solution. See all articles in this series. If you have any particular gripes about what needs to be fixed in iTunes, drop me a line.)

iTunes syncing is a disaster. I’ve written about it several times on this website, and in my articles for Macworld. Following this article – which is the most popular article on my site, every day – dozens of iTunes users have commented about their experiences. And a Macworld article I wrote about this problem has nearly 100 comments.

The frustration level of users unable to sync their iOS devices with iTunes is quite high, in part because they find little or no help from Apple support or Genius Bar. I’m repeatedly told that users who contact Apple hear that the support teams aren’t aware that this is a problem, and users can spend hours doing what Apple recommends – essentially, restoring their device and re-syncing everything – only to find that the problem re-occurs almost immediately.

To be fair, millions of iOS users have no problem syncing. In fact, I’d wager that most iOS users never sync their devices. They download apps, perhaps some music, but keep it all on their devices (which also means they have no backups). But the sync problems seem to arise once users have a substantial media library. iTunes can certainly handle large libraries, but iOS devices seem to be unable to accept them.

While these problems have existed for many years, it seems that they’ve reached critical mass with the introduction of iOS 8. When I briefly had an iPhone 6, I found that, after the first sync, it was nearly impossible to add any new content to it. I get emails almost daily from people experiencing the same issues, with all types of iOS devices, but the iPhone 6 does seem to be more prone to sync problems.

So, two things need to be done. First, Apple has to recognize that this is a problem, and not have their support teams act as though it’s something new and rare. Apple has a history of pretending that nothing is wrong, until they admit that there was a problem. Remember antennagate (“You’re holding it wrong.”), or the video problem with 2011 – 2013 MacBooks Pro, that the company only recently announced that they would fix? They constantly pretend that there’s user error, rather than deal with the issues, because an admission of a problem in their hardware or software would potentially lead them to an expensive recall or replacement program.

Second, Apple needs to fix syncing, period. If you buy an iOS device, you expect to be able to sync your content. If not, the device is simply not fit for purpose. There’s no excuse for selling a device which Apple claims can do all these wonderful things, whereas something as simple as copying music is fraught with so many problems.

It’s clear that none of Apple’s senior executive sync their iOS devices with iTunes. They probably have everything they want in the cloud, and never experience the type of problems that rank-and-file users encounter. I expect that if Tim Cook, Eddy Cue or Jony Ive had this kind of problem with their iPhone, it would get fixed pretty quickly.

20 thoughts on “How I Would Fix iTunes, Part 6: Fix Syncing

  1. BRAVO Kirk for telling the truth, so honestly and so rightfully.

    Apple HAS TO FIX THIS.
    They have the money
    They must assign the necessary resources to have them listen to experienced users, and fix this MAJOR problem for their customers. Period.
    If Apple still cares about their dearest customers, they JUST HAVE TO RESOLVE this.

  2. BRAVO Kirk for telling the truth, so honestly and so rightfully.

    Apple HAS TO FIX THIS.
    They have the money
    They must assign the necessary resources to have them listen to experienced users, and fix this MAJOR problem for their customers. Period.
    If Apple still cares about their dearest customers, they JUST HAVE TO RESOLVE this.

  3. I commented on your earlier article and will again: Hours on the phone with Apple Care, six visits to the Genius Bar, and Apple continued to act as if I had some rare and unsolvable issue with my iPhone 6. Why, they’d never HEARD of any problems such as the ones I was experiencing. In an effort to get shed of me they exchanged my phone for a new one and . . . SURPRISE! The exact same problem. Throughout their suggestion was I use iTunes Match — an impossibility with my large music library. So now I have a 128gb iPhone with a couple of dozen songs on it because to ask it to deal with more than that just causes the whole thing to freeze up and not sync.

  4. I commented on your earlier article and will again: Hours on the phone with Apple Care, six visits to the Genius Bar, and Apple continued to act as if I had some rare and unsolvable issue with my iPhone 6. Why, they’d never HEARD of any problems such as the ones I was experiencing. In an effort to get shed of me they exchanged my phone for a new one and . . . SURPRISE! The exact same problem. Throughout their suggestion was I use iTunes Match — an impossibility with my large music library. So now I have a 128gb iPhone with a couple of dozen songs on it because to ask it to deal with more than that just causes the whole thing to freeze up and not sync.

  5. My wife’s iBook was dying. I figured that there was a micro-sized crack somewhere which, when the iBook reached operating temperature, caused the area to expand creating a short circuit and blank out the screen.

    I rescued everything I could to a USB thumb drive including her iTunes library (much of it purchased), and transferred all her songs to my Mac Mini.

    Now we can’t play any of it since I keep getting a “missing file” error. We’ve tried using her old password, and even tried changing her password in iTunes at Apple. Nothing works.

    Say “Goodbye” to all the music she bought.

  6. My wife’s iBook was dying. I figured that there was a micro-sized crack somewhere which, when the iBook reached operating temperature, caused the area to expand creating a short circuit and blank out the screen.

    I rescued everything I could to a USB thumb drive including her iTunes library (much of it purchased), and transferred all her songs to my Mac Mini.

    Now we can’t play any of it since I keep getting a “missing file” error. We’ve tried using her old password, and even tried changing her password in iTunes at Apple. Nothing works.

    Say “Goodbye” to all the music she bought.

  7. Got caught by this Sunday. The bar chart says I had plenty of space, more than a gig, but I could not delete and add an application that was a wash. Thinking I could get around it by removing my music, I deleted my music only to be told I needed MORE space.

    After an hour plus wasting time, and I did get the application on to the tablet via the store directly. I also got my music back on my iPad and everything else update. But for something so fundamental to an iOS device, I’m challenged knowing this hasn’t captured Apple’s attention.

    I guess they’re out of synch with the issue. (sorry)

  8. Got caught by this Sunday. The bar chart says I had plenty of space, more than a gig, but I could not delete and add an application that was a wash. Thinking I could get around it by removing my music, I deleted my music only to be told I needed MORE space.

    After an hour plus wasting time, and I did get the application on to the tablet via the store directly. I also got my music back on my iPad and everything else update. But for something so fundamental to an iOS device, I’m challenged knowing this hasn’t captured Apple’s attention.

    I guess they’re out of synch with the issue. (sorry)

  9. Just now i am again encountering “Waiting for changes to be applied.” I’m not optimistic. I was syncing an album I bought on iTunes to my iPhone. Some (not all) of the tracks downloaded to my iPhone. Some tracks would not sync from iTunes. I don’t know if they are mutually exclusive. I found a box of manually added songs at the bottom of the Sync Music page that had those tracks. I deleted them from the box, then synced, and they came back. After another failed try, I went into my iPhone and deleted them from there, then synced. I could go on, but the bottom line is that I am once again stuck at “Waiting for changes to be applied.” I see a iPhone restore in my future.

    Thank you for this series of articles.

  10. Just now i am again encountering “Waiting for changes to be applied.” I’m not optimistic. I was syncing an album I bought on iTunes to my iPhone. Some (not all) of the tracks downloaded to my iPhone. Some tracks would not sync from iTunes. I don’t know if they are mutually exclusive. I found a box of manually added songs at the bottom of the Sync Music page that had those tracks. I deleted them from the box, then synced, and they came back. After another failed try, I went into my iPhone and deleted them from there, then synced. I could go on, but the bottom line is that I am once again stuck at “Waiting for changes to be applied.” I see a iPhone restore in my future.

    Thank you for this series of articles.

  11. I seem to be one of the lucky ones who don’t seem to have problems with the basic operation. What about doing something fancy:

    I limit songs on my iPod to 256KBit/second and songs on my iPhone to 128KBit/second. Songs that have a higher data rate take much longer to sync because they need to be compressed first. That’s to be expected. But why can my dual core Mac not use two cores to compress songs, making it twice as fast? Why can’t it compress songs while it is syncing songs that don’t need compressing? Why can’t it be flexible, like the user saying “use 10GB for music” and then it compresses as much as needed to make it fit?

    Surely that’s not too much to ask?

  12. I seem to be one of the lucky ones who don’t seem to have problems with the basic operation. What about doing something fancy:

    I limit songs on my iPod to 256KBit/second and songs on my iPhone to 128KBit/second. Songs that have a higher data rate take much longer to sync because they need to be compressed first. That’s to be expected. But why can my dual core Mac not use two cores to compress songs, making it twice as fast? Why can’t it compress songs while it is syncing songs that don’t need compressing? Why can’t it be flexible, like the user saying “use 10GB for music” and then it compresses as much as needed to make it fit?

    Surely that’s not too much to ask?

  13. I gave up on trying to manage Synching on my 4s. All the music went of and only podcast and audiobooks remain. I don’t know what I will do when the Audiobook content eats up the available storage. The sych would flat out refuse to remove played audiobooks. It flat out refuses to remember how much I’ve listen to either. I’m constantly fast-forwarding through the audiobook to pick up where I left it off before I pluged into the Mac.

  14. I gave up on trying to manage Synching on my 4s. All the music went of and only podcast and audiobooks remain. I don’t know what I will do when the Audiobook content eats up the available storage. The sych would flat out refuse to remove played audiobooks. It flat out refuses to remember how much I’ve listen to either. I’m constantly fast-forwarding through the audiobook to pick up where I left it off before I pluged into the Mac.

  15. I have to say that actual syncing has never been much of a problem for me, as long as iTunes can find the device.

    When Apple introduced syncing over WiFi, I was delighted. I could update my devices from my Mac, wherever they were in the house – or so I thought. Now, how many years later since they introduced this, iTunes still cannot maintain a network connection to an iOS device that is only 6″ from the AirPort Base Station (see, all Apple kit 🙂 when both the iOS device and the Mac have a perfect network connection to EVERYTHING else. This is not an ethernet issue. This is Apple trying to do something fancy over the connection and nothing to do with the underlying protocols. iTunes totally fails to connect 2 devices that have ZERO networking problems. It’s a travesty. Wireless ethernet is hardly bleeding edge technology. How can Apple make such a hash of it.

    I know, Kirk was really referring to the overall sync process, but this is part of it and it baffles me why after all this time, WiFi syncing is still such a dismal failure and I always end up resorting to USB.

    I don’t think it’s just me as my wife has the same problem as do all the friends who I have queried about this.

  16. I have to say that actual syncing has never been much of a problem for me, as long as iTunes can find the device.

    When Apple introduced syncing over WiFi, I was delighted. I could update my devices from my Mac, wherever they were in the house – or so I thought. Now, how many years later since they introduced this, iTunes still cannot maintain a network connection to an iOS device that is only 6″ from the AirPort Base Station (see, all Apple kit 🙂 when both the iOS device and the Mac have a perfect network connection to EVERYTHING else. This is not an ethernet issue. This is Apple trying to do something fancy over the connection and nothing to do with the underlying protocols. iTunes totally fails to connect 2 devices that have ZERO networking problems. It’s a travesty. Wireless ethernet is hardly bleeding edge technology. How can Apple make such a hash of it.

    I know, Kirk was really referring to the overall sync process, but this is part of it and it baffles me why after all this time, WiFi syncing is still such a dismal failure and I always end up resorting to USB.

    I don’t think it’s just me as my wife has the same problem as do all the friends who I have queried about this.

Leave a Reply

This site uses Akismet to reduce spam. Learn how your comment data is processed.