When Jailbreaking Goes Wrong

Last Wednesday, I decided to update my iPhone 3G to the newly released 2.2 firmware. Although jailbreaking is fairly easy and doesn’t require much skills, I am never really excited about doing it as it is very time consuming. What’s time consuming about it you will ask? Well, first, you have to download the latest version of iTunes (I only use iTunes about once a month and I always wait for the next jailbreak method to update it), which always takes a few minutes. Then you have to install iTunes and reboot your computer. Once iTunes is taken care of, you have to download your firmware, download QuickPwn, etc…

Getting Everything Ready

It took me about 3 hours on Wednesday to download iTunes 8.0.2 and firmware 2.2. Why? I have no idea! I have cable so it should be faster but for some reason, it was very sloooooow… Maybe I should have taken this as a warning that it wasn’t the right time to update?!

So here I am, 3 hours later, iTunes is installed, I rebooted my PC, and I am doing one last sync before the big jump. Syncing goes well. Now I am taking screenshot of my springboard and of my Cydia apps. I save these pictures on my computer as it will help me find out what apps and customizations (keyboards, sliders, etc…) I have to reinstall later on. I could avoid this last step by restoring my iPhone from backup and using AptBackup to upgrade my jailbroken iPhone, but I am some kind of a clean freak. I like to start from scratch when I jailbreak my iPhone.

Restoring Vs. Updating

As highlighted by BigBoss, you never want to upgrade a jailbroken iPhone. If you upgrade, you will lose about 500MB of space. If you do that again on the other update, you will lose another 500MB, and so on. This space will only be recovered after a restore. The data loss is because Cydia moves your files around to free up space. The moved files become inaccessible but stay on your disk which means you essentially just lose the space. The solution to this problem is using AptBackup but it failed me in the past so I am not even considering this option anymore.

The iTunes Issue

Everything is now ready. I go to iTunes and hit SHIFT + RESTORE to restore my iPhone from the clean firmware I just downloaded. I choose my firmware and everything seems to be ok as iTunes is telling me it is restoring my iPhone. All the sudden, I get this error message saying that iTunes was not able to restore my iPhone… Oh oh… that’s a problem! Now my iPhone is stuck in recovery mode… I unplug it and plug it back on. Nothing, nada, zip. iTunes doesn’t even detect it. Arrrrrgh! I restart my computer thinking it will help but it doesn’t. iTunes still can’t detect my iPhone. I google my problem and don’t find any solution. I finally remembered that I had read Clay’s post about a similar problem he had when updating to 2.2:

What I had to do was go into Control Panel and uninstall iTunes and uninstall the Apple Mobile Device Application. Then, I could reinstall iTunes, launch iTunes and then connect my USB cord to my iPhone and it finally reinstalled the driver.

I didn’t have anything to lose so I uninstalled iTunes and Apple Mobile Device, and reinstalled iTunes. I plug my iPhone (still stuck in recovery mode) in iTunes and BINGO! iTunes finally recognized it and tells me I have to restore. Once again, I hit SHIFT + RESTORE, select my firmware and everything goes well.

The QuickPwn Issue

At this point, I was really thinking that nothing could go wrong anymore, as I was one step away from being on a clean jailbroken 2.2 firmware. I launch QuickPwn 2.2 and start the pwning process. Everything is doing well until QuickPwn put my iPhone in recovery mode. At this point, I am supposed to wait for QuickPwn to give me instructions to put my iPhone in DFU mode. The problem is that QuickPwn got stuck and wouldn’t do anything. I tried closing and reopening QuickPwn, hoping that it would be smart enough to pick up the process from where it crashed, but it didn’t.

Restoring For The Third Time

It’s been a few hours now that I have started the jailbreak process and I am really over it. It is the first time that I have so much problems jailbreaking but I can’t live without my Cydia apps, so I have no choice to keep going. But first I have to go back to iTunes and restore my iPhone, again, for the 3rd time today. I am naturally very impatient and I was really losing it, swearing in French that iTunes and the iPhone are just a piece of crap. You should hear me swear in French, apparently it’s funny… Ok, so I restore one more time.

Successful Jailbreak

Once I’m restored, I launch QuickPwn again and this time the pwning process goes smoothly. Once done, I go back to iTunes to activate my iPhone. Finally!!! I’m done.

After syncing my iPhone with iTunes, I get all my contacts and apps back. Now I have to configure all my iPhone settings over again. That means configuring everything: email passwords, ringtones, fetch data, screen brightness, international keyboard, etc… This alone took me another 10-15 minutes as my iPhone wouldn’t recognize my work email…

More Problems…

Now I’m launching Cydia to reinstall most of my previous applications. I say “most” as I usually don’t reinstall all of them. Restoring and setting up as a new phone helps me weed out apps I don’t want or need anymore. So I installed pretty much all my apps and decide to launch BigBoss’ FlashLight as a test. I launch the app, verify that it works, and then shut it down. That’s when things went wrong… again. My screen became all dark. So dark that for a few minutes I thought the phone was actually off. When I finally realize the phone is still on, I decide to do a hard reset (home + off button), which didn’t do anything. I reboot my iPhone and the screen is still super dark. I google the issue and read a few posts about how you can sometimes blow up the screen backlight.

Great! It’s 7pm, the day before Thanksgiving, and I am already picturing myself yelling at a “Genius” to get my iPhone replaced asap. I restart my iPhone one more time, and it boots ok! I suspected the problem was from FlashLight and instead of deleting the app, I launched it again, and once again, it turned my iPhone screen all dark. I rebooted a few times and it finally came back to normal. So now I know for sure that FlashLight is the problem so I went to Cydia to uninstall it. I was kind of upset as BigBoss’ FlashLight is my favorite flashlight app. There are 20 similar apps in the App Store but they are not nearly as bright as FlashLight… But I have no choice to install one of them.


About 3 hours after starting the jailbreak process (not counting the download time), I was finally done. All my App Store and Cydia apps are installed, my settings are at my liking, and everything finally works well. In the process I lost many of my “own customization”, which is somewhat annoying. These “own customization” are mostly custom images, backgrounds, unlocker, etc that I edit manually vs. using WinterBoard.

This little jailbreaking adventure made me realize that some people must be very freaked out when this kind of problems happen to them. I mean, I know my way around the iPhone and I got freaked out a few times during this process, so I imagine that someone who doesn’t have my resources could easily give up and take a trip to the Apple Store, taking the risk to be declined any type of help if it is obvious that the iPhone was jailbroken. If there is one lesson I learned from this is that iTunes is a bigger piece of crap than I thought. I’ve always disliked iTunes a lot but now I know that if I have a problem while backing up or restoring my iPhone, all I have to do is uninstall/reinstall iTunes and that should do the trick.

How about you? How was your jailbreak? Let us know in the comments if you had any problem and how you solved them.