Yesterday was not a great day for me technology-wise. Passwords gave me trouble, Windows misbehaved, and the iOS5 upgrade for my iPad was beyond annoying.

However, I learned from my experience, and want to share how I got this done. My mistake was not backing up my iPad before trying to execute the upgrade. I saw there were apps to be updated on my iPad (on the iPad itself) 32 of them. Thinking I should do that, I hit “update all” to those 32. Big mistake. This created “purchases” that were not synced with iTunes (more about that later).

After the looooong download of the iOS5 update, I proceeded to the next step. The iOS5 upgrade told me I had purchases that were not synced with iTunes, I decided to back those up. That appeared to take forever, and I’m not sure if the backup completed, because I walked away at that point. When I came back, the update had failed, and I had to start over again.

Queue that “loop” 5 more times. After getting really frustrated with it, I quit trying. While I was watching Tech News Today on TWiT, I remembered the updates I completed on the iPad earlier. I disconnected/reconnected the iPad, and was told I had purchases that weren’t in sync with iTunes. I had iTunes sync that info.

Then I proceeded with the upgrade, and it took. Took forever, actually. But it took. I didn’t lose any apps or folders, in fact I gained apps that I had taken off the iPad (so those have to be “removed” again). I was a little nervous when I saw “restoring iPad” during the upgrade – at that point, I wondered if people are thinking the upgrade will erase all their “stuff” and they happen to stop it or try to do something else – that could be the reason for additional problems with the upgrade.

I thought Android was cryptic about how to upgrade your phone (using volume up/down keys, the power button, etc.) – Apple doing the same thing with this upgrade. They should really inform the user what is happening, and kick them out of the installation, recommending they sync all their “stuff” before trying the upgrade, rather than rolling another step into the process.

Not everything Apple is as simple as “it just works”. In this case, it takes some time (a lot of time), patience, and not watching for the water to boil. This is what ultimately worked for me, as always, your mileage may vary.