On iCloud Backups

Ever since the feature has existed, I’ve always backed up my iOS devices through iTunes. In the early days of the iPhone, it was the only option. But even in the later years, I’ve continued the practice. That changed a few days ago when Apple shipped iOS 11.4 and enabled the ability to store your messages in iCloud.

It sounds silly in hindsight, but I never liked the idea of paying Apple a monthly fee for additional iCloud storage. Especially if I only needed the extra room to backup my iPhone and iPad. I’ve always had plenty of important data on my Macs and maintaining backups for those machines with Time Machine and SuperDuper! was easy enough.

It seemed like keeping regular backups for my iOS devices through iTunes was a sensible solution. But I was wrong.

In order for a backup solution to be effective, it must be automatic and effortless. Neither of these are true of iTunes backups. And that goes double for someone that has almost entirely transitioned to an iOS-only lifestyle. A few years ago, when I would spend two or three hours each day in front of my MacBook Air, I could at least make an argument. But today, when I only use my Mac for two or three hours each week, I don’t think so.

I tried to mitigate the problem by setting reoccurring reminders in apps like Things, but it was a foolish endeavor. The backup process was too much of a hassle and I would put it off for days. And eventually weeks. Sure, some of my data was stored as iCloud documents or through third-party syncing services. But if something went wrong with my iPad or iPhone, it would have taken me weeks to get back to normal. And I almost certainly would have lost something.

You might point out that iTunes offers the ability to sync over Wi-Fi. And you’d be correct. But in my experience, that feature is spotty at best and fails far too frequently to be considered a reliable solution. Maybe I’m in the minority with this. If it works for you, go for it. But physically connecting my devices with a cable, even seldomly, was better for me than relying on Wi-Fi backups for weeks only to find out that iTunes crashed on day two.

But this past Tuesday, Apple shipped Messages in iCloud and I was finally pushed over the edge. It’s funny how I was willing to put off something this important for so long and all it took was the minuscule nudge of a relatively insignificant feature. Messages in iCloud seemed so sweet, though. It keeps all of your conversations in sync between your devices and can optimize the app’s storage to give your iOS device a bit of breathing room.

Perhaps most importantly, Messages in iCloud was a nifty new feature that I wanted to use. But i had several gigabytes worth of messages data — in order to use it, I was going to need more than 5GB of iCloud storage. And that’s all it took. I opted for the 200GB plan and immediately shared the storage with my wife. Both our iPhones and my iPad are now setup to backup to iCloud and I’ve deleted all of those ineffective reminders in Things.

If not for Apple shipping this feature, I almost certainly would have continued down the path of storing my iOS backups through iTunes and it probably would have bit me in the butt eventually. One of my devices would have wound up broken, lost, or stolen and my most recent backup would have been weeks or months old. That’s an awful scenario on its own, regardless of how quickly I can get up and running again with all of my data. But at least I can rest easy now, knowing that my most recent backup is no more than a day or two old.