iOS 8's iCloud Drive reveals the dark side of empowered users

Apple's iCloud Drive deployment was sure to mess up people's access to documents -- and it did

Apple iCloud icon and wordmark.

When editors at a technology website can't figure out how to set up a basic feature, you know something is wrong. I'm a big proponent of users taking on more technology responsibility, not being subject to the whims of the IT priesthood. But when you become shadow IT or a consumerization user, you're taking on a higher burden.

Yet many people fail to do that. And their technology vendors often fail in helping them do that. Perfect example: Apple's iOS 8 upgrade.

Apple's reputation is all about ease of use and empowered users. But when you upgrade to iOS, chances are very high you'll mess up your iCloud settings and end up with a major compatibility break. That happened to the editors of Macworld UK, who lost their ability to collaborate using iWork documents. It also happened to my far less technical sister-in-law and her husband, who both lost their iPads' iWork documents.

In both cases, the problem was user error compounded by lack of sufficient guardrails by the vendor. This is not an iOS 8 or Apple issue, but if it happens in that environment, you know it'll happen everywhere. Both users and vendors need to step up.

The specific issue is that Apple is changing its iCloud document system at a fundamental level; what had been called iCloud Documents is now called iCloud Drive. iCloud Drive overcomes iCloud Documents' limitation of showing only documents for the app currently open, and it works more like Box or Dropbox in exposing all cloud documents to all apps. Apps still get dedicated folders for their documents, for backward compatibility, but the architecture change is so great that if you upgrade to iCloud Drive, you can no longer sync or share with devices using iCloud Documents.


There's a warning about this when you update iOS, but it's confusingly written, and despite the warning, the upgrade process really wants you to enable iCloud Drive. Here's what my sister-in-law emailed me after all her iWork documents disappeared from her iPad:

A pop-up came up when I tried to use Pages this morning. It said something like upgrade to IOS 8, OK. It would not allow me to use Pages till I said OK, and I was afraid to say OK for fear of losing files or other bad consequences. So I waited for Bob to wake up and look at it. He said OK, then answered another question he can't remember, and that's when the damage was done, he thinks.

Some people have reported that the documents eventually come back if you wait long enough after updating the iWork suite to the iOS 8-savvy version. So far, that hasn't happened for my sister-in-law or her husband.

The underlying issue is that Apple has only partially implemented iCloud Drive -- it's available for iOS 8 and for Windows 7 and later, but not for OS X (that will come with OS X Yosemite's release next month). Lots of people who upgrade to iOS 8 won't know that, so they'll be stuck, as you can't reverse the upgrade. OS X users are especially hard hit, but Windows users must also have the right update, which isn't always automatically installed or easy to find. 

In my in-laws' case, it's likely their iWork documents never were backed up to iCloud to be recovered -- not to their computers, either. One of the promises of iOS is that you can use your device as a stand-alone system, no ties to a computer via iTunes necessary. My relatives use it that way, without iTunes backups. Their farm is also in an area with poor broadband coverage, so it can be weeks before local documents get synced to iCloud, if iCloud sync is even on (they're not sure if it was before the upgrade). Translation: They're mainly local files.

You can blame all this on stupid users, but the real issue is that such upgrades are significant changes that are presented as easy activities -- click the Update button when prompted and you get a "new" iPad, or whatever. As I said, this fooled the editors at Macworld UK, who aren't as naive and trusting as my in-laws.

The truth is that there's a design flaw in Apple's iCloud Drive deployment exacerbated by the trusting self-assurance the consumerization phenomenon advocates and engenders.

The answer is not to revert to an "IT knows best" strategy. IT can be as blind to such changes as anyone, and the technology it picks is often backward. (Don't get me started on how stupid Office 365 is on a mobile device or a Mac, for example. You can't even update your devices list from a mobile device, much less manage any account settings -- not that Windows-hugging IT even knows that.)

I'm not sure what the answer is beyond everyone taking more responsibility for their part of the context. Ironically, the consumerization trend works against that self-responsibility. Here's an analogy: In my 20s, I knew how to change my oil and spark plugs, and it was a fairly simple process. Today, car engines are highly complex and overstuffed with technology, so fewer people can change these items themselves even if they want to. You open the hood and realize it's become rocket science.

Computer technology is making the electronics we use fantastically complicated in the inside but seemingly simple on the outside. We think the equivalent of changing the oil or spark plugs is no big deal -- even OS upgrades are treated as simple, over-the-air activities.

But such changes are a big deal, so we need to learn more before doing it or hire a professional. Most people today do neither. And we'll all suffer for it.