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Mountain Lion’s iCloud puts life, documents in sync

Updated: July 26, 2012 3:08PM

Mac OS X 10.8 (Mountain Lion) has arrived and with it comes iCloud’s make-or-break feature, finally: full, automatic document syncing across all desktops and mobile devices. I can start this column here on my MacBook, go to a coffeeshop, continue working on it on my iPad, use my iPhone to add the introduction that popped into my head while I was getting my car washed, and then come back home and finish it on my iMac...all without having to manually sync or copy a damn thing. Whatever I create or change here is almost instantly reflected on every other copy of that file, physically stored on every other Apple device I own.

And because all iOS devices (and most modern MacBooks with solid-state storage) micro-wake themselves periodically to download updates, I don’t even need to worry about boarding a plane and slipping the surly bonds of Internet access for six hours. I can trust that the documents I worked on an hour ago are already safely on the device. This isn’t like Google Docs.

Apple’s already released iCloud-enabled editions of their iWork apps. As soon as I launched Pages for the first time and chose the “Open…” command, every single column, article, and story I’ve written on the iPad edition of that same app over the past couple of years showed up in the browser window. Within minutes, the sync was complete, and all files were on this Mac and available locally.


And here you see the value of putting most of your life into Apple’s Climate Controlled Pleasure Dome. I switched to Apple’s word processor after I got my iPad, with the benefit that I never have to worry about transmogrifying file formats as I moved between my MacBook and the slate. Now that Mountain Lion has been released, I no longer even need to worry about moving documents between my desktop and mobile devices, via Dropbox or somesuch.

“Holy cats, Andy! Are you saying that all Apple users are going to have to switch to Apple apps from now on?!?”

Settle down, Skeezix: iCloud document sharing is available to all developers who deliver their software via the App Store. They just have to build it into their apps. But it certainly does give a Darwinian edge to apps that exist in both MacOS and iOS editions. And it’s a serious incentive against choosing to sell apps outside of the iTunes ecosystem.

The syncing features of Documents In The Cloud go way beyond what other cloud doc and file services can do...but it has its own limitations as well. The answer to any “Can it do…” question can be found in this statement: iCloud is designed to be a mechanism specifically for syncing data between one person’s many Apple computers.

“If I’m collaborating on a project, can I share my iCloud documents with my other team members?” No; (see: “one person”).

“Will there be a Windows or Android client for accessing my files?” Re: Windows - No; (“...Apple computers”). Re: Android - No; (see preceding, plus: Hahahahahahahaa…..).

“What happens if I’ve got the document open on my iPad, and then I keep working on it with my Mac? Syncing is automatic, so I suppose I would see ghost words appear on the iPad?”

No: if you’re one person, it’s unlikely that you’d be typing on one device with your left hand and another one with your right simultaneously. Instead, a little dialog appears on the iPad informing you that (in effect) since you appear to have switched machines, this iPad copy will close. And as soon as it does, its little file preview in iPad Pages’s document gallery reflects all of the changes you made on your Mac.

(Interestingly, however, the scenario works in reverse. Type on the iPad, and sentences appear on your MacBook, if you’ve left the document window open.)

This example also illustrates some of the big Unsettling Questions of iPad. Pages for iPad is manifestly the Best In Class word processor for slates. But it still doesn’t have the same range of features as the desktop version. And your document might use fonts that aren’t installed on your iPad. What happens if you open a complicated MacOS Pages document with the limited iOS Pages?

Well, what happens is that iOS has to dumb the document down to work within those limitations. And then iCloud will sync those changes back down to the version on your Mac.

Huh. That’s probably not what you would have wished. iOS warns you that this can happen, and suggests that if you’re worried about losing formatting then you ought to open the document as a copy instead of as the original.

OK, thanks for the warning. And the new document will automatically appear back home on your Mac, which is nice. But you’re manually managing versions of docs again and that’s one of the problems that iCloud was meant to solve.

Unsettling Question #2: is iCloud’s syncing 100% predictable?

It all seems to work just fine. Over the past couple of weeks, I’ve created increasingly baroque scenarios to try to trick iCloud into not syncing a doc properly. The one time I leaped from my seat and shouted “J’Acuuse!” before giddily composing a full report on iCloud’s turned out that, um, I had opened two completely different but similar-looking documents.

It was a Layer 8 issue. Which is how IT people say “Meatbags are idiots.”

The Grumpy Old Nerd part of my brain (the part that wishes deep, deep down that every computer were exactly like his first Apple II) would be reassured by the presence of a “Sync Now” button somewhere. But that’s completely unnecessary and Apple was smart to just keep it simple and clean.

Well, then, let’s move on to Unsettling Issue #3: What’s the downside to having iCloud manage your documents?

The news here is slightly less-good. In Mountain Lion, there are two separate but adjoining parallel dimensions for file storage. The standard MacOS Open/Save dialog now has two tabs. “On My Mac” gives you the familiar file picker and lets you navigate your entire hard drive and all attached volumes. You’re not saving and opening documents in iCloud; it’s the classic file system you know, love, and trust. No changes to that at all.

The “iCloud” tab takes the Delorean up to 88 miles an hour and lands you in The Future World Of 2012. You see a curated gallery of all of the documents you’ve created with that specific app. When you open a file, yes, it’s like magic: here’s everything you’ve ever done with this specific app, on every Mac running Mountain Lion and every device running an iOS version of that same app. When you save a file here, bim sala bim, it’s on iCloud, and each of the aforementioned devices automatically receives a copy the moment they realize it’s up there. If you’re not connected to the Internet, no sweat: the file is still saved locally, and it’ll get pushed to iCloud once you’re back online.

You can group documents into folders by just dragging one onto the other, without even leaving the picker.

Fab. But these files are invisible to the main file system, as is your iCloud storage. It’s there on the hard drive, but neither you nor any of your other apps can see it.

Yikes. I mean, you can do a million things with a file if it’s in a Dropbox folder. It’s just a file in a folder. If a file is in iCloud, and you want to do anything with it that doesn’t involve the app that created’re going to have to export it out into the file system first.

To its credit, Apple makes managing iCloud documents as easy as it can be. I can drag files into and out of the iCloud Open/Save box as though it were just a Finder window, and docs can be shared through Mountain Lion’s new Share sheet.

Additional conveniences can, and should, be wired into iCloud-enabled apps. Pages, for instance, has an explicit “Move To…” command under the “File…” menu.

Still, this scheme can be a serious drag at time. Managing a project with multiple assets from multiple apps is so difficult that honestly, you’d be foolish to even try. You shouldn’t use iCloud for anything that can’t be contained within a single least not in this initial incarnation of iCloud document storage.

iCloud documents will indeed show up in a system-wide Spotlight search, but that’s their only incursion into the rest of the Mac experience. In the weeks I spent with the developer prerelease of Mountain Lion, I regularly encountered tasks in which a two-step process expanded into five or six, because of the problems of iCloud’s completely sandboxed file storage. None of those are common things at all, and in the vast majority of situations, I was glad for the convenience of iCloud document storage.

But still, your documents are inside several fortified castles -- fortified, even, from other iCloud app libraries -- and that’s often a drag. The only place where you can even just get a God’s eye view of your iCloud storage is through the iCloud panel in System Preferences. Here, you can see every document stored by every app -- even iOS-only ones. You have a limited amount of free space (5 gigabytes, upgradeable for an extra charge) and this panel lets you delete stuff you no longer need.

Finally, there’s the Most Troubling Issue Of All: What happens when things go wrong?

iCloud’s curation of your files isn’t an issue if you choose to store files locally. And if you do use iCloud, it’ll work great for the majority of your work.

...So long as everything’s functioning fine.

Here’s where I talk about how iCloud and Pages and Mountain Lion failed for me in a major way on Wednesday morning. I finally had the consumer package and walked through my notes to make sure that everything I thought was true with the developer version was still true.

On first launch, all of my Pages docs appeared within Pages, yes, like magic. All went well until I tried to open one of them. Annnd DOWN went Pages. Document after document: instant crash-a-roni, every time.

Is that an Epic Fail for iCloud? Well, not really. I’ve been having intermittent problems with my WiFi all week.

(Side note to my Unnamed Internet Provider: it is unwise to continue to toy with the internet service of an internationally-beloved tech columnist.)

When I re-launched the app, all was well. But it certainly points out the danger of relying solely on iCloud for document storage. If Pages really had decided to spend the whole rest of the day picking blackberries instead of helping me meet my deadline, I’d have been truly hosed. Conceivably, the Pages file I’m working on isn’t available anywhere else except through Pages, and iCloud. If I had stored it on Dropbox, welp, I would have had options. Despite the app’s crashing and refusing to work, my document would still be a file that I could move to another machine, or open with a different app.

And what if things go biblically wrong? I can’t cast aside a serious worry: “Apps corrupt; absolute apps corrupt absolutely.”

Meaning that if I store a file on Dropbox and a file thrashes it, I can just go up to and have the service rewind the file back to its pre-thrashed state. If a bad iCloud app trashes the book chapter I’ve been writing for the past three months — whether by stripping out fonts it doesn’t have or formatting that it can’t deal with, or by corrupting the file itself — the trashed file gets pushed up to iCloud. And then it takes the place of every “good” file on every device I own.

It bears remembering that iCloud doc syncing is still very, very new to third-party developers. Mistakes are inevitable. The current version of DiscoWriter for MacOS is 3.14, and Version 2.03 is out for iOS. What happens if the user falls behind on his updates? He could have 3.1 on his iMac, 3.14 on his MacBook Air, 2.03 on his iPad, and 2.0 on his iPhone. And all of them have access to the same document. If one of these apps messes up the header for that file...bang, that’s four months of work on my novel, gone.

It’s a worst-case scenario, for sure. But four months of work is definitely worth backing up across multiple ecosystems. I worry that iCloud will create a false sense of security. If a file is truly important, then it needs to be exported safely outside of iCloud on a regular basis. And, alas, there’s no simple way to automate that process.

But I’ll wind up by saying that iCloud document syncing is a magnificent step forward. I’ll be cautious about using it for the next six or eight months, but I’ll definitely be using it.

There’s nothing incremental at all about this improved approach to file storage. In 1984, Apple swept aside the text and keyboard model of user interface because it had reached the end of its useful life and needed to die so that something new and better could thrive in that patch of soil.

And file systems require that same kind of revolution. “Files” and “folders” are a metaphor that go back to when accountants wore green visors and arm garters. Training people to understand where their files are and how to access them has only become more complicated in the past decade, now that the damned things can be located anywhere and everywhere...even on another continent.

It’s high-time to strip away all of those unnecessary steps and concepts. It’s time for the OS to step in and make sense of it all. iCloud document syncing is a huge step towards the ideal of never having to care about how, or where, or when, I saved a document. I just sit and work, and my device makes sure that the document I want is on the device I’m using at the time I want it.

Hopefully, we’re seeing the sunset of Volume/Users/Username/Documents/Column_About_iCloud_Docs.pages and the dawn of “Computer, open the Pages doc I was working on last night.”

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