Restoring from iCloud anno 2015

Having an Apple Watch makes me use my iPhone less. I filter and handle notifications on my Watch, and only go to my iPhone to act upon things that really require my attention, or when I purposefully want to browse the web.

Since I now use the iPhone to do something purposeful, either productive or recreational, I love the idea of it having a bigger screen, so I can do the stuff I still use my iPhone for even better or easier. I love the way my iPad works, but it’s not as portable as the iPhone and lacks (in my case) 3G connectivity. If only Apple has an iPhone like device with a bigger screen…

Long story short: I’m currently restoring my iPhone 6 to a new iPhone 6 Plus. (Or hopefully, Apple’s iCloud services are being wonky at the moment…talk about perfect timing.)

Backup and restore

While waiting on things to settle down, I started thinking about how things have changed since I last moved to a new device.

In the first iterations of iOS migrating from iPhone to iPhone meant backing up your device via iTunes, encrypted to preserve passwords, and then restoring that backup to your new device. After the initial restore process finished your iPhone would reboot and it would then start syncing all your apps, media and data to the device. It was easy compared to other smartphones at the time, but it wasn’t foolproof.
iTunes could offer you a corrupt backup making restoring data impossible, your apps would stop syncing halfway through or even if everything synced changes were that all your apps would be in a random order.

Fast forward to 2011 and Apple introduced iCloud backup. iOS devices are now backed up automatically on a daily basis (as long as you have enough storage), and moving from one device to the next is theoretically a single process: make a final backup, shut down the old device, boot the new one, enter your credentials and restore your last backup. No more need to connect to iTunes, it’s an easy over the air process. Theoretically.

There are some caveats though, backups can only be restored to a device that runs at least the same iOS version (with no update option in between), restoring means entering dozens of passwords, and a full restore can take hours. But the device is useable as a phone in the meanwhile, so that’s handy.
As a concept, I’m a big fan of iCloud backup. I’ve used it to move across multiple phones, upgrades and/or repairs it has never truly let me down.

But now, anno 2015, things are a bit more complicated. With iOS 8 Apple introduced Health, iCloud Photo Library and iCloud Drive. They’ve also introduced the Apple Watch. These are all features that are tightly integrated with the iPhone, and in case of the Watch, even depend on the iPhone to function. So before I decided to move to my new iPhone 6 Plus, I wanted to make sure these new technologies would be migrated without any data loss.

So here’s my approach:

iCloud Photos and Drive

iCloud Photos and Drive live in the cloud, so moving to a new device is basically a matter of enabling those services. But before I started the process of backing up my iPhone and restoring the new one, I verified that all photos and files were uploaded, and that they had downloaded to at least one Mac. Just to make sure.

Health

You can back up the data stored in the Health app to iCloud. Your data is encrypted as it goes between iCloud and your device, and while it’s stored in iCloud.
If you’re not using iCloud, you can back up your health data with iTunes if you select “Encrypt iPhone backup” in the Summary tab. – Apple

I’m going the iCloud round so I should be good. It’s a pity I can’t verify this backup until I have restored it to a new device. On that new device you can check wither anything has downloaded by going into Settings > General  > Usage > Manage Storage and see if Health has any meaningful space used. (mine is around 50MB, surprisingly).

Apple Watch

Apple Watch content backs up automatically to your companion iPhone, so you can restore your Apple Watch from a backup. When you back up your iPhone to iCloud or iTunes, your iPhone backup will also include your Apple Watch data. – Apple

Apple Watch requires a backup and restore if you want to connect it to a new iPhone. But compared to the hassles we had to go to to get our iPods to sync to a migrated Mac, the process for an Apple Watch is fairly easy:

  • Unpair (which automatically backups your Watch to the iPhone)
  • Create an iCloud Backup for that iPhone
  • Restore the backup on the new Phone
  • Re-pair your Watch.

Verifying the existence of that backup on both devices is possible by, again, looking at Settings > General  > Usage > Manage Storage > Apple Watch, which will show me the backup file. (around 50kb for me)

Other data

There’s a couple of other things I need to verify, but that haven’t been any trouble in previous restores. All the syncing stuff like contacts, keychain,… is rock solid these days, so that should work.

Furthermore I rely on 1Password for both password and 2FA-storage, so I’m looking forward to testing out the integration of the 1Password extension in so many third party apps. I wonder how they’ll handle 2FA codes, I haven’t seen their extension pop-up in those screens. But either way it should remove a lot of hassle for re-authenticating services like Dropbox or FeedWrangler.

And finally there’s TestFlight. Those apps don’t install from the App Store but from within the TestFlight app so I wonder if they’ll reappear after restoring an iPhone, I’d guess not.

Fingers crossed. Only 25 minutes remaining now.