Why Can’t Apple Fix iOS Syncing?

Here we go again. Yet another problem syncing an iOS device. It’s gotten to the point where syncing an iPhone or an iPad is a perilous task.

Today, I wanted to remove a couple of music playlists from my iPhone and add some others. I checked the capacity bar in iTunes, which showed me that I had a couple of GB of free space.


But when I went to make the change – removing more content than I was adding – I was greeted with this message:


This isn’t like the problems where iTunes suddenly doesn’t recognize the audio files as being music, and shows them as “Other;” this is different. The music is clearly recognized as such, but iTunes – and the iPhone – simply aren’t communicating correctly.

I’ve written about this recently, discussing the huge problems that many users experience syncing their devices. I get lots of emails about this, and Apple’s support forums abound with tales of syncing woes.

I know the solution (which is often just temporary) is to restore the device; to take a couple of hours to copy all my media content and apps. But I’m tired of doing that. I’m fed up with having to do that repeatedly with iOS devices. I really wish Apple would pay more attention to this issue, and fix syncing; or at least offer some guidance as to what’s going on when something like this goes wrong.

I used to think that the ability to have iTunes sync to iOS devices was what made Apple’s products work so well; it has now become the thing that prevents them from working.

Review: Withings Wireless Blood Pressure Monitor

Like millions of people, I need to keep an eye on my blood pressure. You can check it when you visit your doctor, but many people have “white-coat hypertension.” Just getting their blood pressure measured at the doctor’s office stresses them out, resulting in higher than normal readings. All the better reason to check it at home.

A regular arm-worn blood pressure monitor is around $50. So at $130, the Withings Wireless Blood Pressure Monitor isn’t competing on price, but rather convenience. Saving money doesn’t matter if you don’t wind up using the device, and Withings’ version makes checking your blood pressure a lot easier.

Read the rest of the review at Macworld.

iTunes 12 Sync Problems: Why Doesn’t Syncing from iTunes to iOS Devices Work?

Update: See this article for a possible solution to sync issues with iOS devices.

Syncing isn’t easy; syncing a variety of disparate content from iTunes to iOS devices is complex. There have always been problems with syncing, but lately, these problems have increased.

I get lots of email from readers, both of this website and of my Ask the iTunes Guy column on Macworld, and lately a lot of those emails have been about syncing problems. My friend Rob Griffiths had a problem last month where duplicate tracks in his iTunes library prevented him from syncing his iPhone 6. But he’s still having problems; that wasn’t the only issue preventing him from syncing.

I briefly had an iPhone 6. I returned it because of the size, but I had to restore that iPhone about five times in the week I owned it because of syncing issues.

And I’ve had readers contact me with problems syncing older devices; problems that have increased since the release of iTunes 12 and iOS 8. One reader even broke down and updated from an iPhone 4s to an iPhone 5s, hoping his syncing problems would go away; alas, they didn’t. (This makes me think that many sync problems have something to do with iTunes’ library files.)

Syncing isn’t easy; but Apple really needs to make it work. I know that some of the problems are edge cases, but so many people have problems that Apple needs to seriously pay attention to these issues. If you search Apple’s forums, just in the past 30 days, you’ll find dozens of threads about sync issues. Sometimes, the sync simply doesn’t work; at other times, it blocks at “Waiting for changes to be applied.” It’s impossible for users to resolve these issues, and Apple doesn’t provide much help. The general response from Apple is to restore the iOS device. In some cases, this my work, but in my experience, its effectiveness is limited; sync problems come back a short time afterward.

To be fair, it’s possible that this only happens to a small percentage of iOS users. Many if not most iOS users never sync their devices with iTunes, and many others don’t have much content to sync. But Rob Griffiths, who I mentioned above, doesn’t have a large music library. He’s not an edge case at all.

As for me, I had terrible problems in the last months of iOS 7, having to restore my iPhone 5s several times. I’d want to sync to add a new album to my iPhone, and it would take a half hour, and sometimes those syncs would simply fail. Curiously, since iTunes 12 and iOS 8, I’m having fewer problems.

Syncing is hard; but Apple should do a lot more to make it work.

If you have sync problems, I would appreciate if you could post a comment below. I’m trying to collect as much information as possible to try and get Apple to pay attention to this issue. Please post the device you’re using, and a brief explanation of the problems you’re having. Also, post if these problems are new, since iOS 8, or if you’ve had them for a long time. Thanks!

Also, read my series of articles outlining how I’d fix iTunes.

Apple’s iOS Apps are Bloated; and How Many Gigs Do You Get on a 16 GB iOS Device?

I have Apple’s Numbers on my iPhone; I use it because there are a few spreadsheets I maintain to track expenses, and it’s quite practical to have access to them on my mobile device. It takes up 335.9 MB.

I don’t make many videos, but if I did, I might want to use iMovie: it takes up 613.3 MB. And if I were a musician, I might want to have Garage Band on my iPad; it’s 594.1 MB.

It’s quite astounding how much space these apps take up; with the exception of rich-media apps, and the occasional game, they are the largest apps in my iTunes library.

I did an experiment. I have an original iPad mini, and I hadn’t yet gotten around to updating it to iOS 8 (in part because the over-the-air updater told me it needed 4.9 GB in free space, and it’s only a 16 GB device, and I didn’t have enough free space). I loaded it with only iOS 8 and Apple’s apps. I installed all of Apple’s apps: the iWork apps, iMovie, Garage Band, Find My iPhone, Remote, etc.

Here are the default apps, which are installed as part of iOS, and which you cannot remove:


And Apple prompts you to install the rest of their apps (some are pre-installed):


First, those “16 GB” or the iPad mini are nothing of the kind. The real capacity of the iPad is less than 13 GB:

Ember 4.png

Now, this 13 GB figure may be the space available after iOS is installed; but that’s not at all clear, either from iTunes, or from the device itself.

Apple does give some explanation of the storage trickery, about the way the calculate GB:

“When you view the storage capacity of your iPod, iPhone, iPad, or other electronic devices within its operating system, the capacity is reported using the the binary system (base 2) of measurement. In binary, 1 GB is calculated as 1,073,741,824 bytes.

“For example: The way decimal and binary numeral systems measure a GB is what causes a 32 GB storage device to appear as approximately 28 GB when detailed by its operating system, even though the storage device still has 32 billion bytes (not 28 billion bytes), as reported.”

So, is a 32 GB device really a 28 GB device?

This is all the more confusing because, on Macs, they don’t use the same system; back when OS X 10.6 came out, they switched away from the deceptive GB system and went to a real system. So, on my iMac, the 256 GB SSD shows as 251 GB (which takes into account some space, which Apple explains in the above document, for things like the EFI partition, restore partition, etc.)

All of Apple’s apps take up more than 3 GB:


In the end, considering that the iPad shows 1.3 GB of unusable, and unreadable, “Other” space, here’s what’s left, just over 8 GB of free space:

Ember 2

There are several lessons here. First, Apple’s apps take up a lot of space. Installing all of them takes up more than 3 GB out of 13 GB, or 23% of the available space; and that doesn’t count the pesky “Other” space that you can never reclaim completely.

People have pointed out how little free space is available on Android devices; maybe they should do the same for Apple devices. Yes, I chose to install all of Apple’s apps, and I didn’t have to, but, still, Apple prompts you to do this when you set up your device. (And, if I recall correctly, many of them are pre-installed on new iOS devices, though they may not be on 16 GB devices.)

Second, Apple should simply not sell 16 GB devices any more. If, after installing just the basics, there’s only half the advertised space available (I know, I already lost a couple of GB because of marketing), then users can’t put a lot of content on them. Many won’t care, but once you start downloading a few games, you get into a situation where there’s not enough room to apply updates, because they need so much free space. (And, as a commenter pointed out below, Apple still sells the iPhone 5c with only 8 GB; imagine the results if I tried this on one of those devices.)

Finally, the whole thing with advertising a capacity that isn’t realistic – the bit about selling a 16 GB iPad that really only has 13 GB available (after iOS is installed) – is deceptive. I know it’s, in part, because Apple treats bytes in two ways; one as 1024 bits and another as 1000 bits, but you shouldn’t buy a device and take it home and see that it has less capacity than you expect, even if you take into account the size of iOS (and it’s hard to find out how much space iOS actually takes up).

P.S.: Dave Mark commented on The Loop:

“to me, it’s photos and media storage that bring me to my device limit, much more so than games.”

Yes, I didn’t even go there. I wanted to simply look at apps, before a user starts adding music, photos or anything else.

Turn off iMessage for Your Phone Number, Using Apple’s Web Tool

There’s an annoying glitch with Apple’s iMessages on iPhones. For some people, when they turn off iMessages, and switch from an iPhone to another device, it’s impossible to receive SMSs from iPhone users. Something in an Apple database has registered their phone number and won’t release it.

Apple has had to set up a web tool to allow users to free themselves from this blocking.


Go to this page, enter your phone number, then enter the six-digit code that Apple sends to the phone via SMS. Click Submit, and this should update Apple’s database.

This has been an annoying problem for many users, and for a very long time, and, seems to have only found a way to fix it after they faced a class-action lawsuit. It’s good that Apple is fixing it, but I think it’s a bad sign that they’ve had to go the route of a special web page for users to de-register their phones. It suggests that they simply don’t have a grasp of how their own system works, which is supposed to de-register numbers as soon as you sign out of iMessages on an iPhone.

OS X: Prevent iPhoto from Opening Automatically When You Connect an iOS Device, Camera or SD Card

By default, when you sync an iPhone or iPad, connect a camera, or insert an SD Card into your Mac, OS X opens iPhoto, asking you if you want to import photos. I had this setting turned off in Mavericks, but it seems to have been turned on again in Yosemite. Yet when you look in iPhoto, there is no such setting. Tricky of Apple to have hidden it in another app…

Connect your iOS device to your Mac. Open Image Capture, which is in your Applications folder. Click on the iOS device, then you’ll see, below the sidebar, an option allowing you to choose what happens when you connect the device.


(Yes, I have lots of photos of Titus the Cat.)

Click the menu that says iPhoto; you have several options, such as Image Capture, Preview, or, perhaps, other apps. But you can also choose No Application. Select that, and you’re good to go. Personally, I use Dropbox’s photo import feature, then go through my photos in the Dropbox folder from time to time and decide what I want to keep.

If you don’t see the menu below the sidebar, click the little widget at the bottom-left of the window; that will display the menu.

Note: if you’ve turned on Photos in the Cloud in your iOS device settings, you won’t see this option, since your iOS device no longer lets you add photos to iPhoto when it’s connected. And you can’t delete photos from the device using Image Capture either.

Update: a commenter pointed out that there’s a setting in iPhoto’s general preferences. I missed this – in part because I’m pretty sure it wasn’t there in Mavericks – but that setting is global, and affects what happens when you connect any camera or iOS device. In Image Capture, you can adjust this setting individually for each device, so the Image Capture solution is more flexible.

Apple’s iOS Remote App Doesn’t Display Album Art

There’s a bug in Apple’s Remote app for iOS 8. It doesn’t display album art for the currently playing track. It does, however, display art if you tap Up Next.

IMG 2309  IMG 2310

This is a bit annoying. I hope Apple fixes this soon, because I do like to see the album art when I’m listening to music and using the Remote app.

Just another bug in iOS 8…

The AirDrop Mess on OS X and iOS 8

I recently wrote about my problems with Handoff and Continuity features in Apple’s new operating systems. Many people I know have similar problems, and another feature that causes grief is AirDrop. This allows you to easily send files from one iOS device or Mac to another. You don’t have to open a network share, or sign in; you choose whether you want your device to be available to everyone, or just your contacts, and when you’re near another device – within ten meters – you should be able to share files easily.

You should be able to share files. In practice, this is very iffy.

Right now, I have four devices: an iMac, a MacBook Pro, an iPad and an iPhone. They’re all AirDrop compatible.

The iMac seems to work best: it can see both my iPad and my MacBook Pro:


The MacBook Pro can see the iPad (and sometimes the iMac shows up for a while, then disappears). The iPad can see the MacBook Pro. And, most of the time, the iPhone can see nothing, and nothing can see the iPhone.

Right now, as I’m writing this, the iPhone can suddenly see the MacBook Pro and the iPad; but not the iMac. The iMac can see all there other devices, but the MacBook Pro still can’t see the iMac. And all these devices are on the same desk, a few feet apart.

I’ve heard from lots of people who have this problem, along with the Handoff and Continuity problems. The only workaround I’ve seen suggested in to toggle Bluetooth and Wi-Fi, which are how AirDrop detects devices and sends and receives files. Nevertheless, I’ve not found that toggling those makes much of a difference. Devices appear and disappear according to the humors.

It’s important to note that for a device to be detected, it must be on and unlocked. At one point, I thought you had to have the AirDrop window visible in the Finder, but that doesn’t seem to be the case any more (I’m pretty sure it was when AirDrop was first introduced).

The thing is, when AirDrop works, it’s great; it’s a quick way to get files from one device to another. But when it fails, there’s no way of knowing why, and no troubleshooting other than trail and error. In the time it takes to toggle Bluetooth and Wi-Fi on two devices, it’s easier to send a file by email, or via a network share.

This is yet another excellent feature in iOS and OS X that just doesn’t work as it should. At a minimum, Apple should have some way of helping us troubleshoot this. There should be an AirDrop Connection Doctor, as there is in Mail. I can’t help but feel let down every time one of these “magical” features fails inexplicably.

Oh, now that I’m at the end of this article… The iMac can see the iPhone and iPad. The MacBook Pro can see the iPhone and iPad. The iPhone can see the iPad. And the iPad can see the iPhone. Go figure.

Handoff and Continuity Don’t Work on My Devices, and I Can’t Figure Out Why

One of the marquee features of iOS and Yosemite is Handoff and Continuity. According to Apple:

“Continuity features include Handoff, Phone Calling, Instant Hotspot, and SMS. You can start an email or document on iPhone, for example, and then pick up where you left off on your iPad. You can use your iPad or Mac to make and receive phone calls through your iPhone.”

None of this works for me, and I can’t figure out why. I’ll explain what I think might be causing the problem, but, first, here are some of the oddities I’m seeing.

When I get a phone call, it rings on all my devices. I can get text messages from my phone in Messages on my Mac. So that works. But all the rest – the phone calls from the Mac, or any of the document Handoff features – fail.

All my devices are compatible. I have the following:

  • 5K iMac
  • 2013 retina MacBook Pro
  • iPhone 5s
  • iPad Air 2
  • iPod touch 5th generation

According to this Apple support document, I should be able to, say, start an email message on one device, and pick it up on another. But this doesn’t work from any device to any other.

Another oddity is the settings required to use Handoff and Continuity with phone calls. Apple says:

“On your Mac, open the FaceTime app and go to FaceTime > Preferences. Click Settings and deselect the iPhone Cellular Calls option.”

I don’t have any such option:


Nor do I have that option on my iPhone or iPad.

I had a call with Apple support this afternoon, and got transferred to a senior advisor, who couldn’t figure it out. We eventually thought that the only possibility is that my router is blocking something. I use EE for my internet service here in the UK, and use their router (I don’t think you’re allowed to even connect with a third-party router), and then use an AirPort Extreme to distribute Wi-Fi in my house. Yet I asked one friend, who also uses a third-party router in the US; he can get Handoff to work between two iOS devices, but not iOS to Mac or Mac to iOS.

I’m willing to accept that there may be something in a router that could block this feature, though, given its importance, I would have thought that Apple would warn people about it. Do a Google search, and you’ll find plenty of articles saying that it doesn’t work for some people; Apple’s forums have many posts as well.

This isn’t a question of compatibility; all my devices are compatible. But it seems that there’s something on my network that is blocking all Handoff and Continuity features, with the exception of phone calls and SMSs, which may use a slightly different protocol.

What about you? Does it work for you? If it didn’t work and does now, what did you do? I tried toggling Handoff off, then back on; logging out of iCloud, then logging back in (which is an annoying process). Nothing works.

I’m frustrated. This is one of the key features of the new OSes, and it should “just work.”

Update: this whole thing is fubarred… I logged out of iCloud again on both Macs, then logged in again. Now some of the Handoff features work, but not all, and not consistently. (So it wasn’t the router after all.) I turned off my iPhone, then turned it back on, and I new get the iPhone Cellular Calls option both on the iPhone and on Face Time on both my Macs.

This stuff is a mess. The more I’ve looked for solutions, the more I’ve seen people struggling with the same issues I’ve been having. Apple has created a Rube Goldberg that depends on the ever-flaky iCloud back end, and the trouble it’s taken to get this to work – pretty much half a day – is astounding.

It will be interesting to see if this continues working, or if it stops again; I did get phone calls for a while, probably before iOS 8.1. And it will be interesting to see if Handoff every actually works with all the apps it’s supposed to support. In the end, I’m not even sure how useful it is; if my iPad or iPhone is close enough to my Mac, I’m not likely to start working on a document on one of them, then want to switch to another device.

Duplicate Tracks in iTunes Cause Problems Syncing iOS Devices

My friend Rob Griffiths pinged me the other day. He had gotten a brand new iPhone 6, (and ribbed me about it), but was having problems syncing it. He could sync some content, but not movies; then some movies, but not all; then he couldn’t sync at all.

Rob took the extreme move of writing to Tim Cook, one of whose staffers read the email and reacted, quickly. It turned out, as Rob explains, that the problem was caused by duplicate tracks in his iTunes library:

“In the current version of iTunes/iOS, there’s a bug that only appears when you have duplicates of purchased songs. When encountered, a duplicate of a purchased song will (almost always) cause iTunes to silently stop syncing.”

This is interesting, in part because I get lots of emails about problems with syncing iOS devices, and I’d never found a cause. I’m not sure this is the only issue, because sync problems are multifarious. For example, in the few days that I had my iPhone 6, I had to restore it twice, because the device lost track of my music and showed it all as “Other” content. I’ve seen this occur in the past when syncs are interrupted, but this was happening to me with a new device, allowing it to sync completely.

Rob eventually scoured his library with Doug Adams’ Dupin, an app that finds duplicates in iTunes. (Read Doug’s write-up of the story.) I ran Dupin, and was surprised to find that I, too, had a number of duplicates, one of which was a full purchased album by Bob Dylan. I know I had never downloaded that album twice, so I suspect something odd going on behind the scenes in iTunes when it organizes libraries. And Rob is sure that he never downloaded his duplicate tracks twice, but what was interesting was some of them were older 128 kbps tracks with DRM, and some were newer versions; perhaps he upgraded them, at some point, and iTunes didn’t delete the older ones?

What is more likely is that these duplicates were added to his library when he chose to transfer purchases from an iOS device:


I know I’ve done that at times, when I’ve updated apps on my iPhone, for example, and didn’t want to download them again in iTunes (since my bandwidth is limited). But why would it have, in my case, only transferred one album?

I wonder if this is just a bug with iTunes, or with specific iOS devices. Rob never had problems syncing his iPhone 5, and I saw sync problems with my iPhone 6, but my 5s generally syncs without any issues. So there’s some odd combination here causing the issue.

Whatever the case, if you do have sync problems with an iOS device, I’d suggest getting Dupin and scouring your library. It may save you a lot of headache.