iCloud: It Just Doesn’t Work

The promise of Apple, for many of us, is a phrase we’ve all heard many times, “It Just Works.” It’s what we’ve come to expect from their products. They offer us not only an unmatched simplicity, but the confidence in the company to trust in that simplicity. For the most part, this holds true.

My iPod just worked. It’s what led me to buy my first iMac.

My iMac just worked, so I bought a MacBook Pro.

My MacBook Pro just worked, so when the iPhone was announced, I waited in line.

The iPhone just worked, so of course I went for the iPad when it was announced.

And since the iPad just worked, I decided to give iCloud a shot. A service that promised to be the thread between all of these devices. There’s just one small problem. It just doesn’t work.

I’m a big believer in Apple, I’d even go as far to call myself a fanboy. This is a company I want to give the benefit of the doubt to. Theirs is a vision of the future to which I am anxious to subscribe. They are a corporation that I would willingly trust and even pay to store my data. Unfortunately they just can’t seem to give me a service that delivers. As great as their devices are and as great as their software is, Apple has struggled with the cloud. Mobile Me was a nightmare from the start and while Apple seemed poised to redeem themselves with iCloud, it feels as if they’re dropping the ball.

Much like Siri, the few times that iCloud has failed on me has made me wary. Unlike Siri, Apple didn’t ship this as a beta. iCloud was billed their triumphant return to the cloud. Jobs himself acknowledged the shortcomings of Mobile Me during WWDC and promised us that, you guessed it, it would just work.

Well here’s an example of it not working. It a silly one, but it’s mine. I recently purchased Day One, a journaling program that I had just heard too much about not try. The application is available for my Mac and for my iOS devices and uses iCloud as a default to sync entries. It worked perfectly, for a day. Then it suddenly stopped syncing the data on my iPhone. I tried several things to get things going. I turned off the sync and turned it back on again. I even deleted the app from my iPhone and reinstalled it. I still ended up with one entry on the iPhone and multiple entries on my mac. I checked the folder names in iCloud, they were both correct:

The data, not so much:

I even tried to access iCloud through the web to check the folder that’s referenced in Day One and realized that Apple doesn’t even allow users access to these folders:

I only had one option left. Switch from the default option of iCloud to Dropbox. You know what happened? It just worked. Instantly. Even on Apple’s own device with every advantage imaginable, a competitors product worked better. I don’t know if the problem lies with Apple or Day One, I just know that since I switched over to Dropbox, a non-native competitor, things have synced up perfectly:

It’s just an example, but you’ll find plenty of people with their own similar stories as to where they’ve found friction with iCloud and why they are now skeptical. The thing I really don’t get is why Apple decided to bite off so much at one time. By simultaneously launching iCloud for iTunes, Photo Stream, iWork and application syncing, as well as Me.com email, calendars and contacts it feels as if they almost set themselves up for failure. Why not go one at a time? I mean the Mac versions of iWork aren’t even compatible with it at the time of this writing.

Rather than go full steam ahead with all of the aspects of iCloud, Apple would have been far better off starting slow and building back the trust they had lost with Mobile Me. Much like the course I took with my devices, I likely would have followed a similar course with iCloud:

Start with iCloud for iTunes, give me my music, my TV and my Movies on all of my devices. Start with things I bought through iTunes and then go one step further and offer me even more with iTunes Match. Show me it just works.

Next add a photo stream that helps me seamlessly get pictures from my iPhone to all of my devices. I mean, how great would it be to have these all working perfectly with the ability to delete things at launch? Make it just work.

Then launch iCloud for iWork. Let me get familiar with how things work, let me see the benefit of not having access to a specific folder. Let me see that it just works.

Offer me the same option for the data for all of my apps. If it worked great for iWork, why wouldn’t it work well with everything else. You’ve already proved that it just works.

Last but not least, ask for my essential personal data. Everything else would have just worked, so why not this.

Would it have taken longer? Absolutely, but there would have been a far better chance that they could regain my trust. Now, there is little chance that I will ever trust iCloud with anything critical. It will remain my cloud for media, but will likely never be very much more. Apple has always been ambitious, but they almost always wait until something is ready to bring it to market. Everything isn’t always perfect, but it’s almost always ready. Twice now, we’ve seen that this is not the case when it comes to the cloud and I don’t see any reason to give them a third chance.

For a company that executed so well on a long term strategy to earn deep-rooted loyalty when it comes to our devices, it seems as if they either got impatient or cocky when it comes to our data.

It’s really a shame as I’d love to begin consolidating my various clouds. I currently have essential data in Google, Simplenote, Evernote, Dropbox, OmniFocus and keep my media in iCloud. While I like having my eggs in various baskets, this has gotten a bit unwieldy. At first, iCloud showed tremendous potential to help bring much of this data onto the same cloud. Even though there is a good chance that Apple will get their act together and make it so iCloud “just works” I think I’m finally at a point where I just don’t want to try anymore.