"Unable to contact iMessage server": try restoring from iCloud instead of iTunes

I picked up Emily’s SIM-Free [1] 64GB silver 6s from the Mall of America Apple store Friday night. I’d used Apple’s reservation system so that, in theory, I’d be in and out. Alas, Friday night at the Apple Store is a zoo — it still took 30 minutes. The staff were so stressed they didn’t try to up-sell AppleCare or setup a contract — just dropped the box in my hand and ran.

There’s an AT&T store in the MOA and it’s not incredibly busy, so we did our SIM swaps there [2]. My son was going from a 4s to Emily’s 5s, so he needed a new SIM.

I restored both phones from iTunes backups. Emily’s worked, though it was a bit choppy. I had to unlock the phone 1-2 times as it went from 9.0.x to 9.1. 

My son’s restore didn’t work. I completely erased the 5s before starting, but there was still an odd feeling about the way the restore proceeded, perhaps because the 5s was still on 8.x (I didn’t realize it had never been updated).  Yes “odd feeling” isn’t very helpful, but I wasn’t paying that much attention. I’ve been down this road a few times.

Prior to the backup I’d removed iCloud, iMessage and FaceTime from his account, planning to put them on post-restore. I had some trouble restoring iCloud — the phone hung on credential entry. I restarted and it seemed to work — but then iMessage and FaceTime weren’t activated. When I enabled them I got a very cramped non-iOS 9 dialog for entering username and password.

I’ve seen that dialog before. It’s something very old — I suspect it’s hard coded for non-retina screens and dates back to the dawn of the iPhone, pre-iCloud. It’s a bad sign, it exposes Apple’s still broken iOS credential management problems [3]. When I did enter my son’s credentials the dialog hung, waiting for a response. I could kill settings; iOS wasn’t frozen. I let it sit for 15 minutes and it eventually responded with something like “Unable to contact iMessage server”. I don’t think there’s a problem with the iMessage server, I think that’s a misleading error message meaning “something went wrong”.

I called AT&T phone support to confirm the IMEI/ICCID relationship was correct at their end. I’ve had my issues with AT&T, but they must give their support staff very good coffee. They are remarkably pleasant and helpful. AT&T’s configuration looked good.

So either the phone was having hardware issues or something had gone wrong with updating one or more of Apple’s configuration systems. There’s lots of evidence that Apple wants iTunes to “die in a hole”, so I decided to try it Apple’s way. I did an iCloud backup, wiped the phone, and restarted with an iCloud restore.

That went smoothly. During the restore I had my son’s Mac account open for Keychain share confirmation, and I got the usual “FaceTime is using..” dialogs. I didn’t have to enter any extra credentials. iMessage and FaceTime activated immediately.

I suspect the combination of iTunes and iOS 8 to 9 and my removing FaceTime/iMessage/iCloud prior to backup exposed a nasty bug in Apple’s frail authentication systems. The real lesson though is that iTunes backup is seriously deprecated. I’d been moving to all iCloud backup and just doing a manual backup to iTunes every few weeks; that’s obviously the way to go.

- fn -

[1] We are currently AT&T customers, and there’s a case to be made that an unlocked AT&T 6s has the best set of antennae and band coverage for AT&T and even international use. You can’t, however, buy an unlocked AT&T iPhone directly, you have to buy it on plan then pay the plan cost to unlock it. Our AMEX purchase protection and extended warranty only work when the full purchase price is on the card. Hence SIM-Free.

[2] In theory you can move a compatible AT&T SIM from phone to phone yourself, but in practice I’ve seen some odd things. AT&T reps tell me their systems don’t update the ICCID (SIM)/IMEI relationships automatically, or at least not immediately. I think this causes some iMessage/Facetime activation delays.

[3] There are separate credential stores for iMessage, FaceTime, iCloud and the App Store — and perhaps for 1-2 other items. If you migrated from me.com to iCloud.com some of these systems require two sets of credentials. Apple tries to hide this from users, but any number of bugs will expose it.

[4] To fit into the iCloud 5GB limit I routinely delete obsolete backups of old phones and I move Photos.app data to our local machines. I see that with 9.1 there are now more controls on what’s part of an iCloud backup, though they are a bit hard to find.