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Troubleshooting iCloud, Part 1

In part one of a two-part series, Tom Negrino, author of iCloud: Visual QuickStart Guide, 2nd Edition, explains what iCloud is (and isn't) and offers some general troubleshooting techniques that you can use not just with iCloud problems, but with any computing problems you may have.

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Apple introduced iCloud, its cloud storage and synchronization service, to the public in October 2011. By early 2013, more than 250 million iCloud accounts had been created. In my book, iCloud Visual QuickStart Guide, Second Edition, I describe what iCloud is, what it does, and how to use its many services. But one of the subjects that hasn’t yet made it into the book is what to do when things go awry and you need to fix problems with the iCloud service, the data that is stored on iCloud, or problems with data on your Mac or on your iOS devices. In this two-part series, I’ll discuss just what iCloud is (and what it isn’t), so you can properly set your expectations of what iCloud can do for you. Next, I’ll reveal some general troubleshooting techniques that you can use not just with iCloud problems, but with any computing problems you may have. I’ll end part one with some specific iCloud information you’ll need to be armed with before you sally forth to solve your problem. And in part two, we’ll delve into a series of specific troubleshooting techniques, iCloud problems, and how to go about solving them. Let’s get started.

Peering into the Cloud

One of the things I find interesting about iCloud is that, although virtually every user of an iOS device (iPhone, iPad, iPad mini, and iPod Touch) and Mac users running OS X Lion or Mountain Lion has an iCloud account, a surprisingly large percentage of them either have no idea what iCloud really is, or thinks that iCloud can or should be able to do everything that other cloud services can do. For example, recently I saw someone complain on Facebook that iCloud didn’t allow them to simultaneously edit a document with a friend (as Google Drive does). This person thought that every cloud service should have that feature “because that’s what cloud services are.” The reality, of course, is that different services are designed to do vastly different things. So let’s talk about what iCloud is really intended to do for you.

But first, let’s digress for just a moment and consider the concept of “computing.” In just the last few years, things have changed quite a bit from the world in which we were tied to our desktop, or even laptop computers. With the advent of the iPhone and the iPad, you might want to check your mail, add to your calendar, edit a contact, or snap a photo when you’re away from your computer, and if you have more than one computer, or more than one mobile device, it would be nice if changes you made on one device automatically appeared on all your other devices. All of these actions, and the changed or added information that results from them, fall into the realm of computing, but now it can happen almost anywhere.

Essentially, that’s what iCloud is all about. It liberates you from needing to worry about where your data is. There is no wondering about “Did I take my iPhone photos off the phone and put it on the computer?” or “Did I remember to take that appointment I entered on my iPad and put it on my iMac?” With iCloud, these things simply happen, in the background, and you never have to worry about them. Ideally, all your important data and documents are uploaded and stored on Apple’s iCloud servers, then pushed down to all your devices, automatically and seamlessly.

I tend to think of iCloud as “plumbing in the sky.” It doesn’t so much do things itself as it enables devices and software to interact with one another in ways that make your life easier. You won’t be using iCloud to create word processing documents or spreadsheets online (as you can do with Google Drive), or use it to automatically synchronize every document in a particular folder (the way Dropbox does), or save notes and other snippets of information (like Evernote does). iCloud is focused on taking your personal data and synchronizing it to all your devices. So if we take an overview of the different things that iCloud can do for you, you’ll see that it does things that make excellent sense for most of us.

  • Your stuff is always with you. With iCloud, you can wirelessly synchronize contacts, calendars, email, browser bookmarks and tabs, photos, music, apps, documents, and more. You don’t have to “initiate a synchronization,” and you don’t have to do any manual copying, either. All you do is make or edit something, and it automatically appears on the rest of your devices within a few minutes. That something could be making a calendar event or creating a new contact. Or perhaps you snap a photo with your iPhone, get a larger sized view of it on your iPad, and then move immediately to your Mac and touch up the photo.
  • You don’t need to carry all your stuff with you. Most of the storage space used on an iOS device is taken up by music, video, and photos. Many of us have iTunes libraries that are larger than can fit on a mobile device. With iCloud’s optional iTunes Match service, you can have access to your entire iTunes library (including music you didn’t originally purchase through iTunes), and choose what parts of the library you want on a particular device. Because you have more control over what media gets loaded on your device, you can choose an iOS device with less storage space, saving you money. In fact, you don't even need your own device to get to your iCloud data; all you need is a web browser, because Apple has a set of web applications at that allow you to view and work with your information and that are just as powerful as apps on your iOS devices or your Mac (Figure 1).

Figure 1 You can access most iCloud features through the iCloud Web site, where it has a variety of Web apps for iCloud’s different services.

  • Your information is safer, even if you forget. One of the best things you can do with iCloud is have it automatically backup your iOS devices to Apple’s servers, once a day, as long as you have a Wi-Fi connection. So if your device is either lost or stolen, you’ll be able to purchase a replacement device, run through the setup process, and restore from the latest backup, with the least amount of hassle. iCloud can also help you remotely lock or erase the data on a stolen device, potentially saving you from identity theft.
  • Wires? You (mostly) don’t need them. Because iCloud can synchronize many kinds of data and backup your device over a Wi-Fi connection, most of the time you’ll only need a USB connector cable to charge your iOS device. You no longer need a Mac or PC to set up or maintain an iOS device .

Slinging Your Information Around

Because iCloud is focused on synchronizing your personal information, it’s good to know just what information is included. iCloud synchronizes these items:

  • Email
  • Notes
  • iMessages (iMessages are free text messages for mobile devices, and will also work in the Messages app, which replaces iChat under Mountain Lion.)
  • Contacts
  • Calendars
  • Reminders (this uses the Reminders apps in both iOS and Mountain Lion, and works great with devices that support Apple’s voice assistant, Siri.)
  • Photos
  • Music
  • Documents (only if the app has been updated to make use of iCloud for storage)
  • Safari Bookmarks and iCloud Tabs (this synchronizes open tabs on Safari running on different devices)

iCloud is also great at helping you choose the parts of your music and photo libraries you want to share with your devices, using two features: iTunes Match and Photo Stream.

For music, iTunes Match is an add-on service for iCloud, costing $25 per year. For that fee, it scans all the tracks in your iTunes library and replaces them with high-quality AAC files (the same format used by the iTunes Store, with no copy protection). This is great if you ripped many of your old CDs many years ago at lower quality; iTunes Match gives you great sounding versions of the music. Any songs that can’t be recognized and matched will be uploaded to iCloud, and none of this matched or unmatched music counts against your 5 GB iCloud storage limit. The end result is that your whole iTunes library is accessible via iCloud, and you can download any song onto any of your devices. If you stop paying for the service, you get to keep the higher-quality music that you’ve already downloaded.

Photo Stream helps you share photos between your devices and with other people. Photos that you take on any of your iOS devices are uploaded to iCloud, which stores the 1,000 most recent photos. These photos are kept in your Photo Stream for 30 days on a first in, first out basis. Pictures get pushed to the rest of your devices (to save bandwidth, storage space, and possible data charges, iOS devices automatically get lower quality photos), and your Photo Stream is integrated with either iPhoto or Apple’s professional photo editor, Aperture. You can display your Photo Stream on your Apple TV. When Apple introduced iOS 6 in the fall of 2012, they also introduced Shared Photo Streams, which allow you to share selected photos from your Photo Stream with other people.

I haven’t covered everything, but now you have a good idea of the things that iCloud can do for you. Most of the time, iCloud works great, and you should never have to worry about how the service is getting the job done, or whether there are any problems. In true Apple fashion, most of the time iCloud just works. But on occasion, problems crop up, and because your data is stored in the cloud, rather than on your devices, sometimes it can be a little difficult to figure out how to fix things.

Troubleshooting 101

In my family, I’m the designated Tech Support Guy. When things go wrong with their computers, iPhones, or iPads, I’m the person my siblings and dad calls. So over the years, and also because I used to work as a Mac consultant, I’ve developed a method of troubleshooting and fixing problems. This works well with iCloud problems, but you can also use this method for other, general problems with hardware and software.

The single most important rule when troubleshooting is simple, yet surprisingly hard to accomplish: don't panic. Computer problems are frustrating, and oftentimes we feel as if we have very little control over the problem or solution. As you'll see, that's usually not the case. Once you recognize that you have a problem, it's time to take the next step, which is paradoxically step away from the computer or mobile device. You need to take a minute to think through the problem, try to figure out what might have caused it, and make a plan to solve it. In the meantime, it's not going to do you any good to click wildly at things on the screen, hoping for the good kind of lightning to strike. Take a couple of minutes and get past the initial feeling where you're freaking out.

Next, before you try to do anything at all to fix your problem, make sure that you have current, good backups. If you do, then even if it turns out that disaster has struck, you'll be able to get fairly close to your pre-disaster state. If you haven't taken a backup lately, if possible, do it now. You should have been doing nightly automatic backups to iCloud already; if not, connect your iOS device to iTunes and perform a manual backup.

The last preliminary troubleshooting step is really easy. Simply reboot all your iCloud devices, both Mac and iOS. This may sound silly, especially if you noticed a problem on your Mac with your iCloud data, but don't forget that all these devices are interconnected via iCloud. So take a few minutes to completely power down and reboot all the devices. It's surprising how often a simple power-off and reboot will fix an otherwise vexing problem.

iCloud Common Facts

When you have an iCloud problem, it could be in a local device or on Apple's iCloud servers. The devices contain copies of your iCloud data, and Apple's iCloud servers contain another copy of the data, and iCloud's entire reason for being is to make sure that the data is the same at both ends. But that raises an important question: where is the most important copy of your data? The answer is that the master copy of your data is on Apple's servers; everything else is a client to that served data. That leads us to two troubleshooting conclusions. The first is that the iCloud website, with its Web apps, is often the best place to make changes, because changes to your data happen right on Apple's servers, on the master copy of your data, and will be pushed to your devices. And second, if iCloud or one of its services is malfunctioning, you’re going to have problems synchronizing data, and you shouldn’t even try to fix your problems until iCloud is working correctly. You can check to see the status of the different iCloud services by going to (Figure 2). Another possibility for problems--though a low probability--is that the problem you’re having is due to a bug in iCloud or its interactions with the different apps that access iCloud data. I would only conclude this if nothing else you try works to fix your problem, and you’ve also enlisted the help of Apple tech support or the Genius Bar at your local Apple Store.

Figure 2 Check the status of iCloud’s services with this handy web dashboard.

Finishing the Foundation

Now you know just what iCloud can do for you, how to begin the troubleshooting process, and how iCloud’s data works. In part 2 of this series, we’ll dive deeper into specific troubleshooting techniques, iCloud problems, and their fixes.

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