I dot me cloud drive

A few weeks ago, David Sparks was hopping mad about iCloud Drive:

Originally, my ability to sync through iCloud Drive was crippled. My iPhone, iPad, and Mac all had different versions of documents on them despite numerous attempts to reset the system, including logging out of iCloud entirely, switching my .Mac identity to an “iCloud” identity, and even nuking my iPad entirely and starting again from scratch were all fruitless. The most frustrating part is that these failures were not only with third parties using iCloud drive, they were happening with Pages, Numbers, and Keynote as well. How are people at Apple not seeing these problems with their own apps?

Now, for most bloggers, language like this would be no more than the everyday bitching we do when our precious devices don’t work exactly the way we want them to. But for The Nicest Man on the Internet,1 this was a screaming, wild-eyed, spittle-flecked rant. If iCloud Drive drove David to this, I thought, it must really be awful.

Yesterday, David was in a more forgiving mood:

If I had to bet a nickel, I’d say the problem is that cloud stuff between multiple platforms (even platforms you own) is really, really hard. Dropbox and Twitter started small and got big slowly and they had plenty of growing pains along the way. When Apple releases a new cloud service, it immediately has millions of users.

I think Angry David had it right. While it’s true that any new cloud feature Apple offers will be inundated with traffic from its hundreds of millions of users, it’s also true that Apple’s been awful at online services since long before it had hundreds of millions of users. You might say sucking at the cloud runs deep in Apple’s DNA.

When I returned to the Mac ten years ago, Apple was trying to push .Mac, which was the successor to the unfortunately named iTools. The problem with .Mac was that it’s most visible component was iDisk, a utility known primarily for its ability to turn your mouse pointer into a spinning beachball.

Then came MobileMe. It was introduced with the iPhone 3G, just before Apple’s internet-connected user base was about to shoot through the roof. MobileMe will forever be remembered as the reason Steve Jobs called a special company meeting to ask two questions:

  1. “Can anyone tell me what MobileMe is supposed to do?”

  2. “So why the fuck doesn’t it do that?”

For some reason, I got a free introductory month of MobileMe. That one month turned into two and then into four as Apple kept giving out free months as an apology. By the time my extended free ride was over, the service was passable for the one thing I let it do for me: sync my calendars and contacts. And I only enabled that syncing because it was wonderfully convenient when it worked, and I knew I had solid backups when it didn’t. When it came time to start paying, though, I went back to syncing by wire.

The “why the fuck doesn’t it do that?” story came out about a month before the unveiling of iCloud, and there was a faint echo of it in Steve Jobs’s introduction.

I miss “oto-matically.”

Steve wasn’t around to apologize for iCloud. I had syncing problems for a while right after I started using it and then again eight months later, but I had it easy. Many people had continual sync failures. And I’d prefer not to think about developers like Rich Siegel who tried to follow Apple’s rules for syncing their own apps’ data and found themselves in an unworkable mess. There’s a reason Dropbox syncing became ubiquitous among iOS text editors.

And now we have iCloud Drive,2 the service that spun David into a tight spiral as he ended up with different versions of documents on all of his devices. While using only Apple’s own apps.

For ten years or more, this has been the pattern:


APPLE paces the stage in front of a large screen displaying an inscrutable icon.


We’ve got a great new cloud service called N+1! Here’s how it works…


Auditorium event plays on a computer screen with overdubbing in Mandarin. USER 1 and USER 2 watch the screen.


Wow! That looks great! Can’t wait to give it a try!


Wait, remember what N was like when it first came out? Apple always bites off more than it can chew.


Surely they wouldn’t make that mistake again. They got so much bad publicity, they’ll definitely get it right this time.

I’m User 2. I use what I consider the sweet spot of iCloud services: Calendar and contact syncing and iPhone backup. In each case, the huge convenience and timesaving that comes from using the service outweighs the occasional (and by now quite rare) frustration when it doesn’t work.

But I don’t use iTunes Match or Photo Stream. My music and photos don’t need to be transferred instantly. And until we’re another point release or two into Yosemite, I won’t be using iCloud Drive. I’ve seen this movie before.

And stop calling me Shirley.

  1. A nickname due to Gabe Weatherhead that I’m going to keep using until everyone thinks I coined it. 

  2. Well, you may have iCloud Drive, but I don’t. I’m running iOS 8.1.1 on my phone, which is said to be the version that (finally) handles iCloud Drive well, but I haven’t turned it on because I haven’t upgraded my Macs to Yosemite yet. From what I hear, iCloud on one device and iCloud Drive on another is a recipe for data loss. I can wait.