Photo by Gilles Lambert on Unsplash

It’s Amazing That Anyone Upgrades Their iPhone

The ridiculousness of restoring from backup in 2019

I’ve owned every iPhone since the original one back in 2007. Each time that I get the latest version I do something many people consider crazy: I set it up as a new iPhone, rather than restoring a backup of my last device. My rationale is both simple and silly: I like the idea of this being a natural “reset” of my phone — a way to determine which apps I really want, or more to the point, need, on my device. It’s always far fewer than I think. And certainly less than I would have if I restored and deleted just the ones I thought I wouldn’t miss.

Anyway, I bring this up because this process, while in a way liberating, is also a pain. It takes a long time to re-download every app that I actually want. And, of course, even longer to log in to each of these apps. One by one.

And yet I was reminded this week that my process actually isn’t that much more laborious than the more traditional restore. A few weeks back I bought my wife the latest iPhone — she had been using an iPhone 8, and I wanted her to have the best camera to take pictures of our little girl¹ — but she kept pushing off setting it up. When I asked her why, she noted that the restore process is incredibly slow and cumbersome.

Actually, that was my prim and proper translation of what she said. She really just said that it sucks. And I know she’s not alone in thinking that.

This sort of surprises me since I had heard the restore process had gotten a lot better in recent years as iCloud itself has gone from a laughing stock to quite good. And again, doing this all over-the-air sure sounds much easier than what I do each time with a full rebuild from scratch.

But as it turns out, restoring an iPhone does indeed still suck. While you can do everything via the cloud, there are still a whole slew of things that are no better than a clean install. And in some cases, actually worse.

First and foremost, while the restore process remembers which apps you have installed, you’re still downloading them as if you would with a clean install. Second, and most annoying, for many apps, you still have to log in again. Third, some apps think you’re still logged in, but you’re really not, leaving you in a sort of iPhone limbo. Fourth, a bunch of other, seemingly random, data doesn’t cross this transfer chasm, like Health data.

And so I was suddenly feeling a lot better about my process!

But after talking about this on the latest Talk Show podcast with John Gruber, I was reminded that you can also do this restore via iTunes and if you do this via the encrypted method, it will transfer seemingly all of what the over-the-air restore will not.² Great. So that’s what we set out to do this week.

Turns out, not so great.

Backing up the old iPhone in an encrypted fashion via iTunes was easy enough. Though it’s still a comedy of pop-ups when you plug an iPhone into a Mac — hello there, iPhoto! The backup process was pretty quick over cable, taking maybe 10 minutes. This is oddly slower than over-the-air, but again, encrypted, I guess! But when we went to plug in the new iPhone — again, a brand new iPhone XS — we got an error that it could not be restored because the version of the OS on the device was older than the backed up phone.

Apparently the latest iPhone doesn’t ship with the latest version of iOS. Which, fine. I know we’re a few months into the device being out there in the wild. But what’s actually wild is that in order to update it, you need to — wait for it — set up your device as a new iPhone. I’m smiling at this point.

Amazingly, this means logging into an Apple ID account and clicking through no less than a half dozen set up options (Face ID, Apple Pay, privacy notices, etc, etc). Again, this is all just to be able to upgrade a device in order to wipe it again and restore it from a backup.

An hour or so later, we were finally in business, with a working phone from an encrypted backup. Albeit one that was still downloading apps. Sigh. But at least the logins were intact.³

I just can’t believe this is our current state of the art for setting up a new iPhone in 2019. I’m pretty savvy about such things, and I was still confused or dumbfounded by various aspects of the process. I can’t imagine a “regular” user trying to do these things. In a time when Apple is worried about fewer people upgrading their iPhones, I view it as a minor miracle that anyone upgrades their iPhones given such hoops.

I go back to something that Gruber and I talked about on his show. In the move to services, a great one that Apple could offer is the option not only to get a new iPhone at a regular cadence,⁴ but to have it delivered to you with all of your apps installed and working out of the box.

Sure, there would be trade-offs — you’d have to back up your old device the night before and agree that any change until you get the new one won’t be there, or some such — but this could be a truly magical experience. As Gruber noted, it’s similar to what you get when you order a new Kindle and it ships with your Amazon account already set up and logged in.

Yes, the iPhone is substantially more complicated. But again, you’d theoretically be paying Apple for such a service. And it could be a very Apple-like one. Imagine going into an Apple Store to upgrade and walking out with a brand new version of your phone — with all your apps and data — within a handful of minutes. I’m sure this wouldn’t be technically easy. But I’m also sure it wouldn’t be impossible.

And it certainly beats what all of us currently have to do. It’s enough to make you want to set up your upgraded iPhone as a new iPhone each time ;)

¹ We can argue about iPhone versus Pixel here, but the fact of the matter is that she’s fully locked into the Apple ecosystem. If I had proposed her getting a Pixel, I may as well have proposed her getting a landline.

² The fact that you have to this via iTunes, in 2019, like an animal, is… wild! But perhaps changing soon?

³ Turns out, still not all the passwords crossed the restore intact, as Megan found out a few days later… Sigh.

⁴ For some people, every year, for others, every other year, etc.