iPhone Upgrade to OS 3.0
Note: The issues here only affect iPhone developers and only those developers that upgraded from 2.2.1 to 3.0 after they’d provisioned their iPhone.
After WWDC, I setup my iPhone for development use as described earlier. I was running iPhone OS 2.2.1 at the time. Later, I upgraded through iTunes to iPhone OS 3.0 when it came out. I continued the process of teaching my self how to program the iPhone. When it came time to upload a new app, I couldn’t.
After much hunting around, some reading of documents, checking of hex identifier codes, and the requisite gnashing of teeth, etc. I figured out by using the XCode Organizer window that my iPhone wasn’t provisioned anymore. Well as the last real change was the upgrade to 3.0 that was probably it.
I used XCode’s Organizer to “Restore iPhone” (via a popup on the Summary tab) using the iPhone OS 3.0. This wiped the phone’s data and apps and restored it’s provisioning. It didn’t affect the OS version installed. The popup only allowed the 3.0 version to be restored.
This left the phone in a minimal mode only able to make an emergency phone call and with a graphic on the screen that it wanted to be plugged into my USB. So I did that. I used iTunes to re-restore the system to my last backup. Which, fortuitously was five minutes before I started this mess.
In the end, after the few non-productive hours I spend figuring this out, restoring, and re-restoring, I’m back to having my iPhone with all my data, and I can download new apps to it from XCode as well.
The Root Cause
I surmise from past experience in working with keys, certificates, and public key encryption that there is a tie between the certificate and the OS version. This is a pain for developers and breaks Apple’s user experience principle of allowing upgrades without pain. Granted, only developers are affected and perhaps it’s my failing as a new iPhone developer but I had found no warning of this effect of the OS upgrade.
I understand why Apple is using key signing for applications and that’s good. But as a coworker (hi Randy) once said: The point of security is to create a failure point. I would hope Apple tries to smooth this process in the future. An undocumented failure point is more typical of a Microsoft feature than the usual Apple experience.