My dad has a philosophy of never updating to a “dot zero” release until the bugs have been ironed out. In the Windows days, that meant not upgrading to the latest OS until the first Service Pack was released, or just plain not upgrading ever. Today, when Apple released iOS 5.0.1, I told him that the bugs had been ironed out, and that he should update from iOS 4.3.2. Of course, somehow things always go awry when I’m trying to make a point.Pre-Flight Checks
First, since he was running iTunes 10.4, we had to download iTunes 10.5. After that was done, we connected his iPhone 4 and clicked the Update button. Scary Message #1 went something like this: “Some purchased items aren’t transferred, and if you continue you will lose them!” He never synced his iPhone with his Mac, so I figured that the 7 free apps that he downloaded were the problem. I went to the Apps tab and turned on App Syncing, and then hit sync. After the sync finished, Scary Message #2 appeared: “Several items failed to transfer because this computer is not authorized.” So of course I went to the Store menu and clicked Authorize This Computer, and clicked the Sync button again. The sync finished without problems, and I thought we were done. I clicked update, and up came Scary Message #3: “Updating to iOS 5 will delete all the media from your phone!” Yikes. Although I knew that the photos in the Camera Roll would probably be fine if we restored from backup after the update finished, the dialog didn’t make that clear. We opened iPhoto and clicked Import All. After closing iPhoto, I tried the Update button for the billionth time. Wow, it finally started!30 minutes later
iTunes displays a message that it’s going to reboot the device. We go through the on-device setup, and enable iCloud. Scary Message #4 is a modal dialog that asks if we want to merge or not merge contacts with iCloud. I choose “Don’t Merge.” After we get to the home screen, we discover that all the apps are intact, but all his contacts that weren’t synced with Exchange, existing only on the iPhone, were gone. We go back to iTunes and restore the iPhone from a backup at 9:55 PM, the time right before we attempted the upgrade. This time around, we don’t turn on iCloud, so we don’t get the message about contact merging. The contacts are back, but the apps are all gone. Using the Apps pane in iTunes, we restore the apps to the phone, but of course, all the data in those apps are gone.In which I try to use iMessage
After getting the phone in a working state, I decided to play around with some features. I tried to use the iPhone 4 to send a text to my iPod touch 4th generation, because both devices were finally running iOS 5.0.1. I opened the Messages app on the iPhone and selected the New Message button in the top right. I tapped in the “to” field and started typing my name. The suggestions below the field suggested my phone number (for my cheap flip phone that I never use), even though my email address that I use for iMessage was stored in the same contact. I ended up having to send the iMessage from my iPod to his iPhone.Looking to the Future
Really, all of these minor bumps boil down to issues with iTunes and issues with data loss. Supposedly/thankfully, iOS 5 will be the last release where we’ll have to deal with this stuff. When I get around to turning on iCloud (recall that the second time around we didn’t turn it on), the camera roll, contacts, and apps should all be safe from the evil thing known as OS upgrades.