Dealing with iCloud’s Current Shortcomings

I love of the concept of Apple’s iCloud: a system where all my documents and settings are instantly available on any device, without me having to think about configuring sync. If that was how iCloud worked, would be amazing. Unfortunately, Apple’s execution does not equal the syncing utopia I was hoping for.

Problems

My two major problems for iCloud deal with (1) document management and (2) reliability. Document management can be summed up by the “Open from iCloud” dialog box in many iCloud-enabled applications: a list of files in some order.1 My hope is that Mountain Lion’s new folder system will allow slightly better organization for my documents, than a simple list, perhaps with some kind of search functionality.2 For now, however, I am constantly faced with the simple list.

My second problem comes from reliability. I have been a paying member of Dropbox3 for a number of years now and I have never had a problem. When I go looking for ale I expect to be in one place, it’s always there.. With iCloud, however, I have not always had such success. I’ve left work with my iPad a few times, figuring I’d do some work at some other location, only to find that iCloud had not properly synced either the latest version of my document or, sometimes, the entire document itself. This normally means using either Screens or FileConnect to connect to my computer and get the document I need to work on.

Workarounds

In order to work around iCloud’s limitations, I have had to delve into the location iCloud stores documents:4:

 ~/Library/Mobile Documents/

In this directory, there are a number of sub-directories that contain the iCloud documents for individual apps. For example, iA Writer is located in:

~/Library/Mobile Documents/74ZAFF46HB~jp~informationarchitects~Writer

Though the names can look confusing, it is not terrible difficult to figure out which folder refers to which application. Inside the application-specific folder, there is a sub-folder called “Documents” and inside that folder are those documents that are stored in iCloud.

Knowing the location my iCloud documents are stored means that I can create Hazel rules that operate on the folder. These rules are usually fairly simple. For example, I have Hazel sync all text files I create in iA Writer into my nvAlt folder, That way, I can use nvAlt’s full text search functionality to figure out the document name I need to open back in iA Writer. I also use Hazel to create a series of backups of my iCloud documents,5 which gives me a little piece of mind as to whether or not my documents might get lost in transit during an iCloud sync. In total, this series of Hazel rules makes my iCloud experience much more comfortable.

Over the Horizon

Though my Hazel rules have helped me settle into using iCloud for a number of different apps, my hope is that Mountain Lion will mean that they are no longer necessary. Thankfully, I only have to wait another couple of weeks to find out if that is the case.


  1. Most recently edited is the ideal order for me, however, I’m partially okay with there beany order. The applications that seem to just dump the files randomly get deleted from my system rather quickly. 

  2. Byword (affiliate link, as are the rest of the app links in this article) is an example of an application on the Mac that has basic search functionality built into the open dialog box. 

  3. Affiliate Link (the kind where I get additional free space if you sign up) 

  4. This is section is related to how iCloud operates in OS X Lion. My hope is that this workaround becomes obsolete with the enhanced iCloud support in Mountain Lion. 

  5. To my Dropbox account, unsurprisingly.