Notes on an iPhone upgrade

I just upgraded my iPhone 5S to a 6S. The basic backup-and-restore process works remarkably well, as did Verizon’s activation. However a bunch of stuff didn’t carry over. Some of this is my own fault, some of it is security, and some of it is just dumb.

  • Logins. I had to log back in to all these apps like Twitter, Gmail, etc. I’m not using the iCloud Keychain, perhaps that would have solved this. Some apps like Uber, Nest, and TriMet Tickets seem to not work after the restore to new device; the login hangs. It’s not consistent, some apps worked fine. Uber even asked for a password, then hung. I had to delete and reinstall it.
  • Authenticator tokens. I have three MFA tokens on Google Authenticator as well as a separate authenticator from Blizzard. Had to manually set those up again on the new device, which in many cases requires access to the old device’s authenticator. Again I think iCloud Keychain might have helped with this.
  • Music. None of my music copied over. That’s probably because I got hit with another iTunes debacle at some point and iTunes on my computer didn’t have access to my music library. Apple refuses to copy music off of an iPhone, I guess because they think that’s a meaningful piracy prevention mechanism.
  • Cached app data. Some apps cache data locally, like Overcast’s podcasts. That cache seems to have not been copied over. That’s not terrible, but mildly inconvenient.
  • Application data. iOS has a sort of per-app filesystem you can find, where some apps like Wiki Offline store data they downloaded. None of that data was saved or restored. This seems like a serious flaw to me; oftentimes that data is irreplaceable, or at least inconvenient to restore. I ended up copying it over manually.
  • OpenVPN setup. The basic “enable VPN” button still works, so something carried over. But the OpenVPN app was not installed correctly; greyed out for some reason. Also the OpenVPN app has a file in the per-app filesystem I need.