As a tester I’m well aware that things can go wrong during software updates. I always wait at least a week before upgrading iOS on my iPhone, leaving time for issues to be reported and fixed. When I run the upgrade, I’m expecting something to go wrong. This means that I always backup my phone first – luckily!

During the latest upgrade, I saw this on my iPhone:

I’d been expecting something to wrong and my iPhone cable is looking a bit worse-for-wear these days, so I assumed that my phone had been disconnected. Doesn’t that screen look like it’s asking me to plug in my phone?

Naturally I unplugged and plugged in the cable again to restore the connection.

In hindsight I think that image means “iTunes is updating your phone, do not under any circumstances unplug the cable”. From a usability perspective, this image is ambiguous at best. Poor usability combined with my pessimism caused the update to fail.

I’ve had only one iOS update fail in the past, around 2 years ago, yet since then I pretty much expect them all to fail. A catastrophic failure can leave a lasting impression of poor software quality.

A popup dialog said that I needed to run the Restore next which would clear all of my phone settings and restore from backup. That sounded straightforward to me, because I’ve restored my phone in the past with no issues (due to hardware upgrades and replacements). Based only on my personal experience, my impression was that the Restore feature is more reliable than the Upgrade feature. In fact, the upgrade has failed for me just once out of many uses, while the restore has always been successful but I’ve only used it four times.

Then the restore from backup failed, with Unknown error 21.

The dialog with the unhelpful wording led to a website with clear instructions. Some steps were less helpful than others, e.g. Upgrade Windows and reboot your PC.

After following the steps I tried again, and this time the Restore process looked like it was working.

Then iTunes asked for my backup password. I’d just created a backup this morning and hadn’t been asked to give it a password…? I tried my Apple ID password, with no luck.

I found an Apple forum post where someone was complaining about having no way to recover the password. The Apple fan club had gone the offensive, “How could you forget your password? This is your own fault!”. The defence was, “How can I be expected to remember my password from years ago when I bought my first iPhone?”

Aha! A clue… I tried one of my old passwords from days gone by and it worked! The person complaining was more help to me than the Apple-defenders.

My iPhone is now restoring from backup and I’m breathing a sigh of relief. I feel like it could be smooth sailing from here, and there’s only 22 mins remaining.

Now 27 minutes.

Now 34 minutes.

Hmm…