Hey, just so you know ... this post is now about 12 years and 3 months old. Please keep that in mind as it very well may contain broken links and/or outdated information.

The iOS jailbreaking community got a nice holiday/new year’s gift the other week from pod2g and the dev-team: the untethered iOS 5.0.1 jailbreak for the iPhone 3GS, iPhone 4, and original iPad (iPad 2 and iPhone 4S users might get their own jailbreak soon too). I’d been running iOS 4.3.3 on my iPhone 3GS since last May so I decided to take the plunge to upgrade to Apple’s latest software and then re-apply the jailbreak.

To prepare, I made a final backup of my phone with iTunes and also used PkgBackup to backup all of my Cydia apps and data. I also took screenshots of all of my springboard pages so I had a reference of all of my icons, folders, sort orders, etc.

2012 is a brand new year so to start it out fresh, I decided to restore my phone to iOS5 instead of upgrading (in hindsight, this turned out to be a mistake, but more on that later). I let iTunes start the install but kept running into a problem where my phone would hang in DFU mode and iTunes would show a -5000 error.  None of the generic resolutions I was finding on the internet were helping, but after trying a few times the update finally installed and soon after I had a “clean” iPhone running iOS 5.0.1.

Next it was time to jailbreak: I fired up redsn0w 0.9.10b3 and followed the instructions. This part went a lot smoother than the iTunes portion and just minutes later I had Cydia back on my iPhone. I ran into another small problem when I launched Cydia for the first time: it kept saying “cannot locate package” and wouldn’t let me install anything and no applications were found in any of the sources. I tried refreshing the sources as suggested by some internet posts but that didn’t work. What did work was tapping the Refresh button on the Changes tab, though! With Cydia finally working, I re-installed PkgBackup and then restored my backup, rebooted, and re-sprung. My final jailbreak step was to SSH into my phone and change the root password.

Now the full impact of doing a restore to iOS5 instead of an upgrade hit me. First I had to re-create all of my folders and set up my springboard pages (thank goodness I had taken screenshots of everything!) which was a pain since I use FolderEnhancer and thus couldn’t do it through iTunes. Then I had to re-configure just about every app. For some of them I had the foresight to back up their data with DataDeposit so I didn’t lose my saved game progress, but for others I just had to start over (mostly this involved just logging in but it was still annoying). For some reason, though, I lost all of my biteSMS messaging history, even though I saw those files get restored from my PkgBackup backup. I was never able to figure out how to get it back so I had to start from scratch there as well. Also, since my iPhone was completely empty, that first sync with iTunes took a long time as all of my music and videos had to be copied back to the device. Lastly, my voicemail password was lost so I had to reset it through the AT&T web site, which inexplicably deleted my custom greeting so I had to re-record that. sigh

I persevered through the problems and annoyances, however, and now have my iPhone 3GS jailbroken on iOS 5.0.1 and back the way I like it. A few days later I did the same thing to my iPad but this time upgraded instead of restoring and everything went a lot smoother. 😉 Now to learn my way around iOS5 …