So as I’ve talked about before, I have an iPod Touch that I have had since November of last year I think. I love that thing. One of the best toys that I have ever bought. Of course right as I took it out of the box, I did the old 1.1.1 jailbreak and have been jailbroken ever since. I’m currently on version 1.1.3 as I never found a use for upgrading to 1.1.4. Well that was until today.

Today I finally bit the bullet and am going through the upgrade to 2.0 with a stop at 1.1.4 as I’m reading is necessary. I did a backup of my iPod earlier today through iTunes. Not too sure as to what that actually backs up.

I have no problem going “legit” with my iPod Touch. All along I wanted the installer and the apps that come with it as well as the ability to have email on it. I had those via jailbreaking it but now with 2.0, I really don’t feel that I need to jailbreak it anymore. I’ll still investigate what a jailbroken 2.0 iPod can do and maybe I’ll do that too.

Here’s the timeline:

9:30pm – I begin the upgrade to 1.1.4. I have already downloaded the file so it’s pretty fast.
9:36pm – It’s done and I’m happy that I still have my music on there. My home screen is weird because there is only 8 icons on there.
9:38pm – About to start the 2.0 upgrade. Again, I have already downloaded the file and all I have to do is run it.
9:44pm – Uh oh, An unknown error occured (6). Wonder what that means. It’s having me do a restore. I think I read about this a couple of days ago.
9:47pm – Wish I could have stopped it from trying to download the 1.1.4 update. Oh well. I guess I have an extra 5 minutes.
9:51pm – Apparently I should have restored it to 1.1.4 first before going to 2.0 I’ve read. Oh well, maybe others who read this won’t follow my errors.
9:52pm – Restore is going down.
9:58pm – Just was asked about the 2.0 Software Update in big iTunes window. Didn’t see that the last time. Also restoring the backup I did earlier today.
10:00pm – Restore complete now loading back up. Get asked about 2.0 again. Music’s gone.
10:04pm – Going to try the 2.0 update again. While this is going on, anyone subscribed to MobileMe on an iPod yet?
10:11pm – GRR Unknown Error #6 again. I’m stuck in a perpetual screw up/restore loop. At least it knows not to download the 1.1.4 file again.
10:20pm – It just finished its restore and this time my home screen looks a lot cleaner. I still think that I won’t restore from the backup I did this morning.
10:22pm – Didn’t restore from old backup this time. Started fresh. Syncing photos from my computer.
10:26pm – Third time’s the charm right?
10:35pm – I think it did work this time. It’s restarting my iPod. I’m being asked to set it up again or restore it.
10:37pm – It’s even syncing the Twitterific app I downloaded on Thursday for fun. Cool.
10:45pm – Got work email setup with Exchange. Pretty easy. Time to play with App Store.

Overall, this wasn’t a hugely painful process. Sure I had to redo a couple of things a couple of times but I’m happy that I’m legit now with it. I don’t know if I will go back to the pre 2.0 days but if I do, I’ll use this link here from iPod Touch Hacks. They seem to know what they are talking about.

If you have any experiences with upgrading to 2.0 on your iPod Touch, I would love to hear them or share more about what I did.