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iCloud Is Breaking My Mind

By Chris Maxcer MacNewsWorld ECT News Network
Nov 5, 2012 5:00 AM PT

In the history of Apple applications and features, there's only one that consistently makes me feel like I'm an idiot: iCloud.

iCloud Is Breaking My Mind

Apple says it's the easiest way to manage my content -- because now I don't have to. iCloud is seamlessly integrated into my apps and my iPhone and my Mac, and everything just talks to each other and is right where I need it, right when I want it.

The problem is, I can't tell where iCloud begins and where it ends. I can't tell when it's working, when it's not working, and when I've just selected the wrong setting. Consequently, my experience is not anywhere near Apple's vision, not even close to Apple's promises.

Wrong Hemisphere

If Apple's iCloud is a Hawaiian paradise, I'm in Siberia. It starts with trust, and right out the gate I started off on the wrong foot with Apple. Why? Some idiot at Apple thought every picture I took on my iPhone ought to be broadcast out into a Photo Stream -- or automatically appear on all of my other devices. Really? With iOS 6, Apple corrected the Photo Streams issue so that you can share your photos only with those who you want to. (This is good because if you're a congressman, the last thing you want is the private photos of your junk getting broadcast out to your constituents.)

When Apple first introduced Photo Stream, I never used it. What if I am shopping for a birthday gift and I snap a photo of a gift I want to research and then boom, it shows up on Photo Stream? But now with Shared Photo Streams, I can still share photos by creating Photo Streams on the fly -- and only let certain people see them.

Looks Simple

That's cool. It's not so hard. Except, to join a Photo Stream -- that is, to see the photos I'm trying to share -- you need an Apple ID and iCloud. Seems simple enough, right?

It's not. What about grandma who wants Halloween photos? What about kids? What about spouses? How many Apple IDs and iCloud accounts do we have to have anyway?

Let's walk through this.

For starters, Apple seems to assume that all of our i-devices are under our own control -- even while at the same time it shows families happily sharing and using iPads and iPods. Right now, if I turn on my Photo Stream, every photo I take, every screenshot I make, every photo I import, gets transferred to my iPad, and who knows who could be holding that at any given moment. All your photos get sent to an iPad that wanders around the house. Your kids could use it, they can delete things, they can hand it to the neighbor kids. Now, I'm a tame guy. I don't take wild photos with my iPhone, but still. Automatic photo transfers are great when you control all the endpoints. iPads, however, are shared devices.

Share and Share Alike

Next, let's consider the Apple IDs. Does a married couple need to have two Apple IDs? Two credit card accounts? Sort of. The benefit of a shared household is that you shouldn't have to buy multiple copies of every app, song, or movie you want. If I buy a movie, my wife sure as heck ought to be able to watch that movie on her iPhone, too, right? It seems simple, but it's not.

I have to have Home Sharing turned on, and that's associated with my Apple ID. Now add a new Apple ID to the mix, and even if I sync my iPhone with my Mac and backup my wife's iPhone to my Mac, and let her also have songs that are on my Mac on her iPhone, suddenly you end up with situations where just to update an app, you have enter in the password for the original Apple ID, as well as enter in your own ID. All the freaking time, it seems, because my iPhone 5 has to communicate with Apple just about every time I want to browse the App Store.

It seems as if my iPhone has a sick, needy relationship with Apple. Call me. Call me again. No, really, tell me you love me and that everything is OK. Are you there? Yes. Good. I miss you. Tell me you love me again. Every few times I use my iPhone 5 with iOS 6, it seems like I'm getting prompted for my Apple ID password.

Share Me Maybe

Because of all this, I can see where a household would want to just have one shared Apple ID, one account for iTunes and the App Store, and share the content that's purchased. Except, that means, for example, that a dad is suddenly subjected to all the painful pop songs small children buy, like "Call Me Maybe," which is akin to taking a guy's brain to a cheese grater and rubbing violently. It goes both ways, though. There are plenty of Kid Rock songs that do not need to show up on a child's iPod.

So, now you need multiple Apple IDs and iCloud accounts. OK, again, seems simple enough -- but guess what, if you don't have your own shared photo stream enabled, you'll end up with a pop-up window that says, "Shared Photo Stream is not enabled. Review your iCloud account information in System Preferences." You can click Cancel or Review. If I click Review, I then have to navigate through the preferences on my Mac to select Shared Photo Streams -- but not My Photo Stream, because if I do that, all my photos will get transferred all around to my different devices, and we've been over that already.

The first time I tried to walk through all of this and share a Photo Stream, what happened? After trying to join the Photo Stream to see the shared photo -- because I'm going to have to explain all this to family and friends, mind you -- what kind of message do I get? An error message. No kidding. "An error occurred while joining the Photo Stream. Please try again later."


That's it. I'd prefer if Apple was little more personable with its error messages: "Hey, buddy, something went wrong and we don't know how to explain it to you because we're not sure what the problem is, or if we do, we don't want to admit it, and if we do know, we don't think you're smart enough to understand anyway. But heck, if you want to, you can try again later, maybe."

Imagine Your Important Documents

iCloud is far more than just sharing photos. You can also use it to sync documents that you're working on, and app developers can use it as a backbone, too. Except, again, what document are you working on and who's suddenly trying to color with fingers on your iPad at home? Is your report getting messed up by children? How is that secure? Ooh, and let's see, how fast can a child email out your unfinished report to your entire contact list?

How about Notes and Reminders? These two apps are great. I start a note on my iPhone and boom, I'll see it on my Mac. That's cool. But I don't have Notes on my iPad for all the reasons implied above. The same with Reminders. When I have a small and controlled ecosystem, iCloud is more doable. Yet, I'm not always sure if iCloud is getting tapped or not -- or even when there's a setting that I'm missing or misconfigured or if there's failure. The problem with things that are seamless and invisible it that it's hard for a person to understand what the heck is going on.

So far, for me, reviewing iCloud, much less putting it to work, is a daunting, painful endeavor. Every time there's an error, I shy away from using iCloud. Every time I get some message that doesn't make sense, I hate iCloud and my iPhone.

Vanishing Problem

Earlier this summer, I had iTunes on my Mac telling me that my playlists were iCloud playlists and were no longer resident on my Mac. This problem seems to have gone away, I don't know when or how, but I do know that I used to have to fight iTunes and my iPhone to get playlists and songs to play. It breaks a guy's trust, I'm telling you. Sometimes you just need to rock out to some Sick Puppies, and when it's unavailable, it's irritating.

More recently, I thought I had a playlist on my iPhone with songs intact, but when I was on an airplane and tried to play those songs, "Oops, sorry," my iPhone seemed to tell me mid-flight, "Those songs weren't really on your iPhone because you can only stream them, and since you don't have a cellular connection or WiFi right now because you're on a plane in airplane mode, you can just try to drown out the noise around you with your mind, not your songs." In this situation, I didn't even get this explanation because I could see the playlist but when I tapped a song to play it, nothing happened and I was returned back a level in the Music app.

Apparently, I'm an idiot because none of this seemed obvious to me in the airport.

There's a lot more to iCloud, though, and I find much of it maddening at best and utterly confusing at its worst.

Not the Apple You Expect

Apple products should de-clutter your life and make everything easy, fun, and seamless. Instead, I end up fighting iTunes for control over a playlist with songs that I always want stored on my iPhone, physically there, never streamed from iCloud, as I said above. I'm fighting mad and want to throw my iPhone at the wall, but then iCloud works. I buy a song on iTunes and magically, even though I haven't synced my iPhone to my MacBook, I can play the song when I'm out and about. Nice. That's awesome.

Then I go into my Videos app and there are two Rob Thomas videos that won't ever leave my iPhone. I can't delete them. They are in iCloud, permanently attached to me from my purchase history and I can't make them go away. I can delete them from my Mac, but they are still on my iPhone, as an iCloud downloadable item. Have you ever bought something from iTunes and now you hate it so much that you want to forget it exists? I have. But iCloud dooms you to remember all the stupid things you bought or downloaded in your past. At least with a stalking girlfriend, you can get a court order to keep her away from you. The only way to do it with Apple and iCloud is to create a whole new Apple ID identity and try to erase your past and start fresh.

This isn't just a problem with your iPhone. When I use my Apple TV, I have old TV shows that I bought years ago that I will never ever watch again, like "Jeep World of Adventure Sports" or some such nonsense. They clutter up my experience, and I can't delete them. Is this the power of iCloud? That curse of having to have access to everything you or your family downloaded from your account? Lego Ninjas? Where did that come from? Who put it there? When? Thanksgiving? I have no idea.

But this cannot go on. I'm an Apple fan. My iPhone 5 is with me wherever I go. I can't continue futzing around with iCloud. It's untenable. I must figure it out. To do that, I'm going to have to break it down, feature by feature, and try to follow the paths. It's going to take some time, and I'll try to create useful reviews of the pieces and parts along the way.

In the end, I'll have a stronger iCloud, iOS, and Mac experience.

Or I'll be off the grid because I thew my iPhone into the street then ran out in traffic so I could stomp it into oblivion.

Right now, as I attempt to wrap my head around all the iCloud pieces and parts, the odds are 50-50 at best.

Stay tuned for iCloud Review Part 2.

MacNewsWorld columnist Chris Maxcer has been writing about the tech industry since the birth of the email newsletter, and he still remembers the clacking Mac keyboards from high school -- Apple's seed-planting strategy at work. While he enjoys elegant gear and sublime tech, there's something to be said for turning it all off -- or most of it -- to go outside. To catch him, take a "firstnamelastname" guess at

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