This article originally appeared in TidBITS on 2014-10-15 at 4:49 p.m.
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Moving to iCloud Drive

by Michael E. Cohen

When iOS 8 came out last month, those of us who installed it found our iOS devices asking us whether we wanted to upgrade to Apple’s new iCloud Drive service. Adam Engst advised that “when iOS 8 asks you to upgrade to iCloud Drive, tap Not Now” (see “iOS 8 Users: Do Not Upgrade to iCloud Drive [1], 16 September 2014).

Why? At the time, OS X 10.10 Yosemite was presumably a month from release, and 10.9 Mavericks was incompatible with iCloud Drive. Also, as Adam put it, iCloud Drive is “a one-way street — once you upgrade, you can’t go back to the old document-and-app-specific approach that’s compatible with Mavericks.” Users not running a developer preview or a public beta of Yosemite would find their iCloud documents inaccessible on their Macs if they accepted iOS 8’s kind offer. Particularly annoying, though, was that the same day that iOS 8 debuted, all the iWork Web apps at made iCloud Drive a requirement.

This left users who used iWork apps on their Macs, their iOS devices, and in their Web browsers facing a dilemma: no matter which way they went — whether enabling iCloud Drive or not — they would find one of their avenues of getting iCloud documents blocked. The matrix of accessibility was complex.

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That was then.

Now Yosemite has descended upon us from on high, and the time has arrived when the majority of Mac and iOS users will want to revisit Apple’s iCloud Drive upgrade offer. As an early adopter (with the scars to prove it), I have already done that: a week ago, I installed the “golden master” of Yosemite on my iMac. With that final piece in place, I enabled iCloud Drive.

In my case, I had no choice but to do it and hope for the best. I need to revise “Take Control of Pages [4]” to match the new iCloud Drive reality that Apple has imposed on us. Fortunately, the transition went well… for the most part.

What Worked -- As I expected, my iWork documents appeared in the iWork Web apps on just as they had before the transition. Moreover, also offered a new iCloud Drive file browser that made managing iCloud documents much easier.

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Pages for Mac also took swimmingly to iCloud Drive, employing a new, much more Finder-like dialog for opening documents, with sidebar items for accessing Pages documents in iCloud, any document in iCloud Drive, or any document on the Mac.

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And, of course, the Yosemite Finder made iCloud Drive an equal citizen with all of my Mac’s local folders and mounted volumes.

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As for my iOS devices, my aged iPad 2 and new iPhone 6 Plus presented my iCloud documents as they always had in my iWork apps. For those apps, on my iPhone and iPad at least, the transition was transparent, though it did take a number of minutes for each of the devices to sync documents with iCloud Drive (I have about 60 Pages documents in iCloud, some of them rather hefty).

What Didn’t Work -- My iPad Air, on the other hand, was not so lucky. At first, the documents in the Documents browser in Pages seemed to be syncing with iCloud, but not very well: some synced, some didn’t, and some stalled midway in the syncing process. In fact, those documents that stalled never finished syncing. Moreover, if I changed a Pages document that had synced to my iPad Air, those changes never synced back to iCloud Drive.

I tried to convince my iPad Air to accept the iCloud Drive updates in several ways, all to no avail:

(Note: it’s very easy in Yosemite to back up your iCloud Drive documents to your Mac — in the Finder, just drag them from iCloud Drive to a local folder.)

Anyway, three strikes and I thought I was out — that is, I figured my next move would be to completely wipe my iPad Air and set it up as a new device.

Fortunately, before I took that drastic step, I tried one other thing.

What Solved the Problem -- What finally got my iPad Air to join the iCloud Drive party was this: I signed out of iCloud on the iPad Air (Settings > iCloud > Sign Out) and then signed back in.

Signing out got rid of all my iCloud data on my iPad Air (including shared photos, contacts, and so on, as well as the documents in my iWork apps). My iPad Air and iCloud (not just iCloud Drive but all of iCloud) had become complete strangers.

Signing back in reintroduced my iPad Air to iCloud, and, in the process, my shared photos, contacts, and everything else iCloud-related all synced with the device — including the documents in my iPad Air’s Pages app.

Now I have iCloud Drive working on my Mac, in my Web browser, and on all three of my iOS devices. When I make a change to an iWork document on any of my devices, those changes propagate quickly to my other devices (though not instantly — it sometimes take a minute or two for an updated document to sync on another device when I open the iWork app on it). Once again, everything just works.

Yosemite is now upon us, and if you are an iCloud user and you upgrade to Yosemite, you won’t be able to avoid iCloud Drive. In most cases, your documents should weather the transition intact, but if you also have an iOS device and you discover that iCloud Drive misbehaves on it in any of your iCloud-enabled apps, do the simplest thing first: sign out of iCloud on the device and then sign back in. This simple act might well brighten up an iCloudy day.