Murphy’s Law is a law, and it struck once again today. I’m leaving on a week long trip to the south of Spain the day after tomorrow, and tonight my iPhone decided it was the opportune moment to stop working. I went for a walk downtown, came back, put the iPhone on my desk, and a few hours later my Watch suddenly showed the ‘No Phone Connected’ warning and my iPhone simply refuses to turn on.

I’ve tried all the normal troubleshooting: push the power button for 30 seconds, push both home and power for a minute, connect to a power source,.. but all to no avail. Worse, if I connect the iPhone to my battery pack, it doesn’t even seem to be charging.

Which means, if I want a working cellphone during my holidays (or a camera, walkman, maps, travel documents, books,…) I either need to get it swapped tomorrow, or buy a new one. And since there are no official Apple Stores in Belgium, and a reseller swap takes a full working day, the only option is buying a brand new iPhone and getting this one repaired in the meanwhile.

Aside from this logistical — by lack of a better word — problem, I also have a bigger problem: against all rules and common sense I’m running iOS 9 on my iPhone, and I’m not so sure iOS 9 currently makes iCloud Backups: My iPhone always displayed an error when I checked its status. My Mac does show a recent iCloud backup from two days ago for the iPhone. But chances are, I’m going to start from scratch this time. Which would be the first time since.. iPhone OS 1.

Thanks to iCloud and other cloud services I won’t really lose any data. Practically all my data sync via iCloud or proprietary services (hello OmniSync!), so aside from manually downloading all apps and rearranging the homescreen, historically there’s never been any really date left that only exists on the device. I say historically because since iOS 8 this has changed.

With iOS 8 Apple introduced us to Health. And thanks to Apple’s rigorous Privacy policies, this data never leaves the device and is only backed up in an encrypted iTunes backup or iCloud backup. So if you start from scratch there’s no way to get your existing data back to your device. Secondly, iMessage is easily configured, but there’s no cloud based platform for this service, which means any device that’s restored from scratch can’t download your conversation history.

And thirdly, the Apple Watch is dependant on your iPhone, and its backups live on your iPhone.  And, you guessed it, they are once again backed up via iCloud Backup. Start from scratch and you lose your Apple Watch configuration.

So basically a user who loses his iCloud Backup, due to stupidity (me), a bug in Apple’s software (me) or some obscure error, can’t recover a lot of his or her data. Which makes me wonder: on what basis does Apple decide what they sync and can easily be recovered, and what they see as static data that can only be backed up?

  • Option A: The “across devices” angle: everything that lives on multiple devices should be synced. But iMessage lives across their platform and does not sync old data back to a new device.
  • Option B: The privacy angle: everything that’s personal is locked on your device. It’s only backed up and doesn’t sync. Health and iMessage contain a lot of personal info and I can see how syncing can increase the changes for privacy breaches. But then again, iCloud Keychain is the key to all your personal data, and that one syncs.
  • Option C: The device angle: what lives on one kind of device stays on that device. People tend to have only one iPhone. Both Apple Watch connectivity and Health are unique to the iPhone. So not syncing them seems logical from their standpoint. But iMessage is, again, an exception to that rule.

In the end, if you lose your iCloud Backup, you lose a lot of data that you wouldn’t lose if those apps used the regular iCloud file syncing solutions. I see no reason why apps like Podcast or News do sync via iCloud, and something like Health doesn’t. Especially not in a world where two-factor authentication and trusted devices will be fully integrated in iOS 9 and El Capitan.

Either way, I hope I can restore some backup to my new iPhone tomorrow. Fingers crossed and to be continued. And since I’ve learned my lesson: my temporary iPhone will be a cheap one, and will become a dedicated testing device.