Of all the iOS 5/iCloud announcements made during this summer’s WWDC, the one that excited me the most was Documents in the Cloud. Unfortunately, it’s also turned into the one that disappointed me the most at launch, thanks to a number of issues.


Of all the iOS 5/iCloud announcements made during this summer’s WWDC, the one that excited me the most was Documents in the Cloud. Unfortunately, it’s also turned into the one that disappointed me the most at launch.

Documents in the Cloud is a way to sync documents and data across your devices. While it may seem like it takes the place of iDisk, it doesn’t replace it. There is no Finder-like access to a file structure. Each app has its data sandboxed, so it’s app-specific. If you open the same file in Pages and GoodReader, and tell each to upload that file to iCloud, you will have two copies of the file up there.

Setting up Documents in the Cloud

The initial setup of Documents in the Cloud is very easy. On your iOS device go into Settings, then iCloud, and make sure Documents and Data is set to “On.” You can also tell it to not sync when only on cellular networks.

To use the iWork apps with Documents in the Cloud, you’ll need to be running the latest versions of Pages, Keynote, and Numbers. The first time you launch each of these apps, you’ll be asked if you want to use iCloud. If you choose to use iCloud, any local iWork documents you have will be uploaded to iCloud, so don’t worry about losing them. However, once you enable iCloud, you will no longer be able to use iTunes to add a document to an iWork app. Using “Open With” from an e-mail still works just fine.

Syncing between iOS devices

Right now, syncing between iOS devices is Documents in the Cloud’s strong suit. Changes made to a Pages document on my iPad show up within seconds on my iPhone. As a control, I performed a worst-case scenario for syncing: I deleted Pages from all my iOS devices and reinstalled it on my iPad. All my files were still there.

This service isn’t limited to just iWork, as games like Scribblenauts Remix will let you use iCloud to sync your saved games between devices. GoodReader for iPad also supports iCloud. The GoodReader for iPhone update is still in Apple’s review queue as of this writing.

Syncing between Windows and OS X

This is where Documents in the Cloud starts to fall down. While there is a Documents and Data checkbox in the iCloud Preference Pane in Lion, I can’t tell where the data is saved to. I also doubt it’s user-accessible.

The only way to get data from my Mac to iCloud right now is via the iCloud.com website. Unfortunately, the only apps that show up on the website are the three iWork apps. The good news is, you can upload and download either iWork or Microsoft Office files from here. The bad news is, if you have PDFs on your Mac you want to get into GoodReader and iCloud, there isn’t an easy option outside of iTunes syncing (that still works for GoodReader).

There are APIs available for developers to use on Windows and OS X that hook into iCloud. My bet is in the long run developers that want to make it easy for users to put data into their apps. Omni Group has said the next version of OmniGraffle for iPad will support storing documents in iCloud, but I don’t see any mention of OmniGraffle for OS X and iCloud. Omni Group tends to be on the leading edge of development, so I’m curious how they will handle this.

Final thoughts

Buyer Beware

I had little faith in iCloud retaining my data during yesterday’s craziness. My tests on seeing if a changed document was properly updated on the web and iOS were successful. However, at least three times when I went back to look at something on the web interface, my documents were gone. I would either have a web page empty of documents or one prompting me to get iWork for iOS. The first time this happened was during the afternoon and I was having trouble updating the apps. I thought maybe one of the apps got rolled back and threw iCloud off. The second time I had noticed my iPhone wanted to download the update again (I think I had deleted it) and I thought maybe something had gotten wonky again. The third time I didn’t do anything. I went to the web page, saw no documents and opened up Pages for iPad and watched three documents delete themselves.

Problems are ongoing. When I create a new document in Pages on iOS, it prompts me to either create a document, or import one even though iCloud is specified in Pages’ settings. This is how Pages worked pre-iCloud, and turning iCloud on and off doesn’t fix the problem.. When this happens, both the iPhone and the iPad can’t see iCloud. At which point I thought to myself: Yep, these are the guys that brought me MobileMe. It’s possible it’s related to all the iCloud launch issues, but I’m very scared to trust it with my data.

These issues aside, until there’s an easy way to always update documents on a Mac or a PC, Documents in the Cloud is of limited use to me. I’m not optimistic this is going to happen any time soon. All of Apple’s promo videos that show iWork on iOS being used with iCloud never show a Mac as part of the chain (the Mac does feature prominently when they demonstrate photo stream). I also don’t like that third-party iCloud-enabled iOS apps can’t register themselves on the website so you can drag files to them.

I was really hoping I would be able to round-trip files from OS X to iOS without doing the download/upload two-step. It didn’t seem like a fantasy to work on a document on OS X Pages, close it, and head to diner and have it magically appear on my iPad. Until Apple and other developers use those OS X and Windows APIs, that fantasy won’t come true.

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  1. I was really cheesed yesterday when I discovered that Documents in the Cloud–the one feature to which I was really looking forward in iOS 5–made me jump through the extra hoop to copy documents from iCloud back to my Mac. Perhaps I was naive in assuming my MacBook Pro was a ‘device’, yes, but that feature has gone from one I highly desired to one I’ll likely never use.

  2. dropbox, here I come.

    And what’s up with Apple’s anti-folder fetish?

    “There is no Finder-like access to a file structure. Each app has its data sandboxed, so it’s app-specific.”

    I can’t imagine having to scroll down thousands of files to find the right one. And most times, I group related pages and numbers files within an easy to identify and convenient folder.

  3. If the numbers app on the cloud worked on my imac & macbook as it does on my ipod touch, it would be perfect. That would be this . . . .
    1. See document, open it.
    2. make changes, close it
    3. The changes are synced on other devices.
    As it is, the simplest path I have figured out for macs is.
    1. Sign into icloud on a browser.
    2. See document, download it.
    3. Make changes.
    4. Upload it to iCloud, where changes show up on other devices.
    5. Either save or trash modified downloaded document.

    I still have not wrapped my mind around the versions thing, no save as, and other aspects of the new protocols with Pages and Numbers. I am assuming there is some overall big unified paradigm Apple is presenting here. That said, if it is so, speaking for myself, it is not intuitive in the least.

  4. On a Mac your iCloud data files are accessible at ~/Library/Mobile Documents

      1. Yes, it does. Just make sure you make your Library folder visible first. Please stop crying about it: all files are fysically in the directory Y mentions.
        I really don’t understand all the disappointment. iCloud does exactly what was said it would.

  5. “ScubatankmanThursday, October 13 2011
    dropbox, here I come.”

    Dropbox rocks! Seamless integration between OSX and Windows. I am definitely not trusting my important files to iCloud just yet.

    On a positive note though; iCloud seems to be working great with Outlook. My contacts, reminders, and calendar are all running perfectly. Apple may have actually gotten it right this time after the MobileMe embarrassment. :)

  6. Not sure if it’s just server overload but the Docs sync just NOT working today at all… I’ve got different quantities of docs in every iWork app on my iPads and iPhone.

  7. I absolutely agree with your post. I thought I had done something wrong and I have been searching the settings. I also discovered that a movie I stored in the cloud from GoodReader if deleted from the cloud using the Mac iCloud management controls in OS X preferences immediately gets deleted from GoodReader which is not what I wanted.

    IMHO (Mac Book Pro + iCloud) + (iPad + iCloud) = iCloud (FAIL)

  8. It’s actually very easy to transfer files in GoodReader via iCloud. There is a folder called “icloud” on top of the file list in GoodReader, say for instance, on my iPad. I copy the documents that I want to transfer into this folder. Then, on a different iOS device, say my iphone, I open GoodReader, select the files, and download (select >> because the download option is on the second menu page). That’s it.

  9. Thanks for the article. iCloud is by far the most disappointing roll out by Apple. You would think idisc functionality would be replicated in iCloud.
    Going to drop box.. never looking back. If this is the mark of the beginning of the “post-Steve Jobs” era, I’m not looking forward to the years to come.

  10. Great review. I have a question. Did anybody noticed that the Mobile folder on a mac keeps an exact replica of the files on the cloud, no matter if you tell either Keynote, Pages or Numbers to store the file there? I am a bit troubled, wasn’t this supposed to be “on the cloud”

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