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Practical Mac

The “cloud” should remove the anchor that keeps us sitting in front of a particular piece of hardware, whether computer or mobile device, to access a file we need.

Apps in the cloud, such as Google’s popular Web apps, mean we didn’t have to install software to have access to relatively sophisticated programs. But data are another matter.

Apple’s iCloud was announced more than a year ago as the next generation online data system for Apple, replacing MobileMe, which had replaced .Mac, which had replaced iTools. iCloud would have a few Web apps for handling email, working with appointments, and viewing and changing contacts. But it would serve as a robust back-end for programs to sync data and make it available across multiple devices registered to the same account.

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While iCloud launched a year ago October, most of its document benefits remained unrealized until Mac OS X 10.8 (Mountain Lion) shipped in July. The launch version synced data (including photos) across iOS and 10.7 (Lion) systems. It also included iOS backups, allowing restoration of an iPhone, iPad, or iPod touch.

What Mountain Lion fully enabled is what’s called Documents in the Cloud, a feature by which Apple’s own productivity apps (Pages, Numbers, and Keynote) work neatly with iCloud document storage. Some other programs had beaten it there, including Smile’s PDFPen and PDFPen Pro (

In Pages ($19.99) and other Apple apps, the Open dialogue box appears with two buttons in the upper left: iCloud and On My Mac. Click iCloud and you see any files saved to iCloud from Pages on any iOS device or Mac that use the same Apple ID account with iCloud. Click On My Mac, and the traditional file-navigation controls appear. Any changes made in iOS or on the Mac flow back to all the other devices. (iOS apps don’t support all of the features in Pages and other Apple programs, but ignore the elements they can’t modify.) Unsaved files in Apple’s programs are automatically backed up to iCloud, too.

Behind the scenes, what you see as iCloud is, in fact, a special folder hidden in the user directory that Mac OS X keeps synchronized with the iCloud service, sending updates and downloading modified parts if a file is in use on another computer or device at the same time. If you make changes at the same time on, say, an iPhone and a Macintosh to the same file, the version that’s saved first to iCloud becomes the most recent version. It can get complicated.

Files stored in the cloud can be moved to a Mac and vice versa. In Pages, hovering over a file’s name in the title bar for a moment makes a downward-pointing arrow appear at the name’s far right. Click that arrow, and the options Move to iCloud and Move To appear. Move To lets you select a folder accessible to your computer. Move to iCloud relocates the file in the hidden iCloud folder and starts syncing it with Apple. While you can view files stored via the iCloud website, they may only be downloaded, not edited.

This reveals a problem with iCloud sync that’s not at first apparent. After saving or moving an item to the cloud, it can only be accessed by that program, whether in a Mac or iOS version. Edit a photo in Preview and save it to iCloud and then try to use it in Pages in a newsletter? You have to move the photo to your computer in Preview first.

It’s not like Dropbox, Google Drive, and Microsoft SkyDrive (see accompanying story), but application-specific file synchronization. For neophyte users or for particular documents this makes sense, but may frustrate veterans like myself.

iCloud isn’t trivial for developers to add to their software, although many have and many are attempting to make the transition. For instance, Yojimbo (, a portmanteau storage program into which you can place text, encrypted notes, PDF files, Web page archives, and more, lost its sync option when MobileMe was shut down.

The developer, Bare Bones, has been working to move to iCloud, but programs that use a database to manage data, as Yojimbo does, are difficult to rework around the way Apple synchronizes records.

Further, Apple allows third-party software to work with iCloud synchronization only if the software is sold via the Mac App Store. The App Store is a built-in marketplace found in Mac OS X, but it includes only software programs that Apple has vetted and then approved for sale.

Outside developers don’t have to sell through the App Store in Mac OS X, unlike in iOS where all apps must be bought or downloaded from Apple. iCloud offers the only distinct advantage for third-party software developers (beyond, for some firms, the added marketing value Apple provides).”

But there are workarounds. Smile’s PDF editing and viewing software can be purchased from its site or from the App Store. If you purchase directly from Smile, you may buy a 99-cent “connector” app from the App Store that provides the conduit to and from iCloud and meets Apple’s rules. Smile’s approach doesn’t work for all apps.

Apple includes 5GB with a free iCloud account, and adds additional amounts for a fee. For a yearly fees of $20, $40, and $100 Apple adds 10GB, 20GB, and 50GB to the base 5GB.

I use iCloud for backing up my iOS devices and iTunes match, which counts nonmatched files against iCloud storage totals. That pushed me into the additional 20GB category.

Apple has a way to go for iCloud to be as widely used for documents as it is for other kinds of sync.

The company built a narrow definition of file synchronization that appeals most to users who don’t want to manage which file lives on what computer for a particular piece of software.

Glenn Fleishman writes the Practical Mac column for Personal Technology and about technology in general for The Seattle Times and other publications. Send questions to More columns at

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