I eagerly started the download and update of my iPhone 4 to iOS 5 as soon as I saw it was available.  After all, Mashable said in its review that “The final release is one of Apple’s most polished yet.”

Apparently the iOS 5 update was going to back up phone, then clear my content and settings, upgrade the phone to iOS 5, and then restore my content and settings.

When I saw that, my first step was to do a manual backup of the phone before proceeding.  I did the backup in iTunes, selected the “Restore from Backup” option and it gave me a nice list of previous backups including the new one dated today at about 2pm my time.  I was all set to start!

I ran the upgrade process, and it automatically did its backup and started a “restore” of what I assume refers to the iOS 5 software, i.e. an installation, not really a restore.  However after a few minutes, it failed with an error:

iOS5 Upgrade Error 3200

And yes my real name is “Paul”. Hi! I pressed the “More Infomation” button and it did not know what a 3200 error was but suggested 5 or 6 steps to try to resolve the problem.

I thought “surely most people’s upgrade works, so it must be something different about my phone or configuration”. So I thought the best way forward was to make my configuration the simple case: a fresh iPhone.  I had the 2pm backup, so I could reset my phone to defaults, removing my content and settings.  This went smoothly, but after clearing the phone, I was still getting the error above.  I tried repeatedly varying different things, like shutting down all the running apps that I could on my host PC, nope, restarting the machine, nope, and I saw on the Mashable review comments that others were getting the same 3200 error.  Finally reread the “More Information” page again, and one thing I had not yet tried was disconnecting all other USB devices.  Well I left my keyboard and mouse plugged in, but I did have an USB-based UPS providing emergency power if needed, and an external USB hard disk connected.  I disconnected both and tried the update yet again.  This time it did not get the 3200 error!  Yay me!  However when it tried to “restore” the backup it had saved, there was a new error:

What the heck?  Given there was nothing to go on here, and no More Information this time, I decided it was time for some voodoo repair.   When in doubt, reboot.

After rebooting, I wasn’t getting any errors syncing from iTunes to the phone, which was now running iOS 5. So far so good.  Now the only problem was that it was a blank phone, missing all my content and settings.  Time to restore that 2pm backup!

What 2pm backup?WHAT 2PM BACKUP??? There was one for 3:13pm, when it had automatically backed up my EMPTY phone.  But it looked like iTunes had replaced my good backup with the newer empty phone.

This is where, as a developer, I have a real hate-on for Apple sometimes. That dropdown list above… the one with no scrollbar… the one that appears to have 8 items to choose from… well there are more in the list.  But Apple, in their infinite wisdom, seems to have chosen to only show me the most recent from each backup date.  Or something, not sure what. But it would appear to be a filtered list!  Of backups?  Are they trying to cause a heart attack?  [Update: It’s not filtered. It’s just brain-dead. See below.]

I was starting to freak out a bit, concluding that I would have to restore the 8-month old backup from February… even though I know I do backups much more frequently than that.  But being a keyboard kind of guy, I scrolled down through the list with my keyboard down arrow key.  And the 2pm backup was there!  I didn’t ask any further questions, I just selected it and started the restore.  And it seems to have been successful.  Phwew.

So I’m backup up with iOS 5 and all my recent data and settings.  Somehow.  But I can’t help but think that one wrong turn above and I would have lost everything.  I just fluked into getting through this.  Thanks Apple for making it so painless.  And thanks Mashable for calling it “polished”!

Update 1: Apparently the 3:13pm backup *is* the 2pm backup. What? Yeah.  Once you select it, it reports the backup time in the line below the selection.  When I scrolled using the keyboard, I saw the 2:05pm appear much to my relief and just did the restore.  But when I dropped the list down, I only so the other (wrong) time for each backup.  Whatever that is.  So what’s in the list?

iOS5 Backup Timestamps?I guess I just have to add this to my long list of problems with iTunes, a software application which probably represents one of the worst user interfaces of all time, from a company that usually excels at great user interface.  Maybe it’s just me that would be confused by this — the guy with the Bachelor of Computer Science with Specialization (BCSS, Software).  Maybe I need a Masters in software to be able to use iTunes.

Update 2: The nightmare continues.  I went to http://www.apple.com/icloud/setup/pc.html to download the iCloud control panel applet for Windows:

The “Download now” link apparently takes you to a Knowledge Base article… that is completely blank. Really. View page source shows that it’s actually completely empty.

Helpful KB Article