My Epic Jailbreak Fail, and How You Can Learn From It

Tis the season of newly untethered jailbreaks, so I figured I would go toe to toe with this formidable foe and see how I stack up. While everyone else was busy watching the big game on Sunday, I was locked in my own battle of wills, and it was a battle I won’t soon forget. Hopefully in reading this article, you can avoid what happened to me.

The games began on Sunday afternoon, as I set out to upgrade my iPhone 4, which had been jailbroken on iOS 4.1, to 4.2.1 and to jailbreak it again using the newly released version of Greenpoison. I am not new to jailbreaking, by any means, but you wouldn’t have known that if you saw me melting down at the keys of my laptop Sunday night through Monday evening. I have actually been jailbreaking my iOS devices since my first gen iPhone over three years ago, but that didn’t keep me from looking like a rookie this time out. Instead, I found myself spending hours hopelessly mired in the mud of fail. And I have to admit, it all started because I tried to take a shortcut. I’ll take you through what I did, and where things went wrong….multiple times.

The Prep Work- A Good Start
The key to winning any type of battle is to start with a solid game plan. Well, I actually managed to do that before I kicked off my little misadventure. I started by backing up EVERYTHING. I work as an applications engineer and dabble in IT for the company I work for, so I am a stickler for having multiple redundant and reliable backups. I’ve learned the hard way just how important having these is. If you’ve spent much time around iOS devices, then you know how severely lacking iTunes device backups are, especially when problems arise. With this being the case, I made sure to take further precautions, which ended up saving me a lot more potential headaches at the end of this whole mess.

The first thing I did was to sync all of my apps that link to cloud services. For example, I have Pocket Informant synced to Google Calendar and Toodledo. Docs To Go, Evernote, Laridian’s PocketBible, and Olive Tree’s BibleReader are also examples of apps that have methods of syncing information to cloud services or remote servers.

Doing this insures that any data you have recently entered is stored remotely, so you can get it back if you run into problems.

The next step was to take advantage of any apps that have a built-in method of data and/or settings backup.

Some apps backup to the cloud, some allow you to offload files to your computer by running a web server on your phone, and others allow you to get files out through iTunes’ built-in file syncronization. Some of these apps would include the aforementioned Pocket Informant and PocketBible, as well as the popular database app, HanDBase. Unlike iTunes backups, these are files that you can access and control individually, and that is always the best way to backup an app when available.

If you are already a jailbreaker, you may already be familiar with a couple of free apps that I used to help this process along. AppBackup and AptBackup are both jailbreak apps that help you get beyond the constraints of iTunes. AptBackup simply makes a list of the jailbreak apps that you have installed, and stores it so that it becomes part of your iTunes backup. Once you are done with your upgrade, you can jailbreak, re-install AptBackup, and then have it re-load your jailbreak apps. It doesn’t actually back up any data, but it is a handy thing if you use several Cydia apps. Well, at least it used to be. More on this later.

AppBackup is the real MVP of this contest, as it gives you the ability to backup the internal data for any installed app from the App Store. Simply scroll down the list of your installed apps, and select which ones you want to backup.

When you are upgraded and jailbroken again, re-install the app, and all of the data for any app the you backed up can easily be restored in a matter of seconds.

You don’t have to use AppBackup on every app you have installed, as many of them, such as the Facebook app and Twitter clients, are simply pulling all of their data down from the web. It is meant more for apps like games that have save files that you want to keep, or apps with lots of on-board data or settings that you want to preserve.

There are a couple of weaknesses in AppBackup’s game, however. First of all, there is no export feature built-in. If you want to get your backup data off your iOS device, you will have to use SSH to get in and copy it out. Second, you have to be careful of backing up certain types of apps. AppBackup backs up everything in the app, which is no big deal 99% of the time. However, you shouldn’t use this on GPS apps with on-board maps, such as Navigon, TomTom, or Magellan, or any large games, such as FIFA 11. AppBackup uses file compression, but it will still add 2/3 or more the size of the app to your storage, which can eat up your free memory quickly. Thankfully, if you run into trouble with storage space, you can delete any of the backups that you choose from within the app.

For those few apps that were too large to use AppBackup on, I just went to my bench, and used the freeware program WinSCP to log into my iPhone’s file structure, find the apps in the database, and manually copy over the necessary files. Fortunately, I only had to do this for Navigon MobileNavigator and CoPilot Live, but it was still a pain. If you are following along here, and you also have to SSH into your iOS device, you might want to go ahead and grab your AppBackup files while you are at it, just for safekeeping. They are located in /var/mobile/Library/Preferences/ AppBackup/tarballs, for future reference.

My last step was to take screenshots of each one of my app screens to record their setups. This ended up being a REALLY good decision that helped me salvage some points at the end.

The Upgrade- And So It Begins….Badly
So, after all of that, as well as the obligatory iTunes backup, I was ready to get started. Here is where things started to go off track. As the best laid plans often do, mine quickly went awry, allowing the Jailbreak to jump out to an early lead. When I started the upgrade process, all looked to be going smoothly at first. I then ran into the iTunes 1013 error, which I have actually seen before. This is a common issue, experienced by many jailbreakers. I have used the TinyUmbrella desktop utility to make backups of my SHSH blobs in the past. I didn’t run it this time, as I already had my 4.1 blobs backed up, but it still ended up causing me some grief.

TinyUmbrella uses your Windows (or Mac) Host file to spoof your computer into thinking that it is communicating with Apple, when it is really talking to their server for the purpose of backing up your blobs. Unfortunately, the program doesn’t clean up the changes to your Host file after it is finished. That means that the next time you try to run an Apple upgrade, you get the 1013 error because you can’t see their server for firmware signing verification. After searching Google and refreshing my memory on the last time this happened, I opened my Host file in Notepad and manually cleaned up the Apple entry. After that, the upgrade to iOS 4.2.1 sailed along just fine.

After this experience, I am wondering whether I will use TinyUmbrella going forward. Cleaning up the Host file isn’t a big deal, but it a hassle when you forget to do it, or why you have to. When you only jailbreak every few months, it can be difficult to remember this step. Considering that Cydia backs up your blobs automatically once you are jailbroken, I think I will just stick with that until TinyUmbrella is updated to automatically clean the Host file after backups. Fortunately, with my solution to the 1013 issue, I managed to come up with a defensive stand, but still gave up an early lead.

Jailbreak 3 – Me 0

Turning it Over
After getting past that relatively easy issue, I plunged headlong into my first big mistake. If you read the published instructions from any experienced jailbreaker, they will tell you that when upgrading a device that is already jailbroken, you should restore it as a new device after your upgrade to the latest version of iOS. (Note: This only applies to currently jailbroken devices. If you are just upgrading a stock device, you can restore from your backup, as normal) This takes longer, as you will have to go back and re-enter all of your settings, but it is a safer approach since no previous jailbreak artifacts will be reloaded onto your iOS device and cause issues and instability.

Well, expert that I am (cough, cough), I decided to ignore that advise and restore my previous backup to save time. I figured that, with my previous jailbreking experience, as well as all of my data backups, I could get past any potential issues. Considering that I spent around 8 hours over the course of two days in front of my laptop working my iPhone through assorted issues, that didn’t really work out for me. While I cannot definitively say that this decision was the cause of my problems, it certainly didn’t help. As much time as I ended up spending on this jailbreak, I wish I had just gone ahead and done it by the book. This is what coaches call shooting yourself in the foot.

Jailbreak 10- Me 0

The Restore- Round 1
After my early setbacks, I finally got back in the game. The restore of my backup to the phone went smoothly. All of my phone settings were transferred, and my app data was preserved. However, my Apps “disappeared.” More than likely, this problem was caused when I restored from a jailbroken backup. Like the 1013 issue, I had seen this before, as well and I was ready. Remember those screen captures? This is where they become a life saver. Instead of having to reconstruct my familiar layouts from memory, I had a trusty guide to do it by, which saved me a lot of time.

After all of my music and photos had synced over to the phone, I used iTunes’ App tab to select each app to restore and place it in the appropriate page, in the correct location.

Sure, this took a while to do, as I have over 100 apps installed, but at the time it seemed better than the alternative of setting the entire phone up as new. All of my app data and settings were already preserved without having to restore from AppBackup, so I was happy and back in the game.

Jailbreak 10 – Me 7

Unfortunately, the celebration didn’t last long. For the first of three times, I would get extremely close to being finished with the process, only to see the whole thing unravel. It was after the big game on Sunday night, at this point, and I was actually finished rebuilding all of my screens. All but two of my apps were synced over properly, and had all of their data. For some reason, BibleReader and CoPilot Live were having some issues and generating errors when they attempted to sync over.

I figured the best solution to this was to just bypass them in iTunes and reload them from the App Store later. I unchecked the sync boxes for the two apps, and synced iTunes one last time…or so I thought. When the sync was complete, all of my apps were still there on my phone, but all of the folders that I had spent all that time creating had been stripped out. I went from five screens to twelve, with my apps in completely random order. I was definitely NOT happy. It was already getting late, and I had to redo all of that work of rebuilding my screens. I had to have my phone ready for work in the morning, so the work had to be re-done. All of the momentum now belonged to Jailbreak.

Jailbreak 17 – Me 7

The Wipeout- I Was SOOOOOO Close
I finally finished my second pass at my home screens after 1 AM Monday morning. I then decided to go ahead and jailbreak the phone. At that time, I thought I would be in the field for work on Monday, so I figured it would be a good idea to install MyWi in case I needed it for tethering. The jailbreak with Greenpois0n hung up on the first attempt, but went through fine on the second try. I then installed Cydia without any issues, and decided to call it a night. Despite all of the early setbacks, I am still in this thing!

Jailbreak 17 – Me 10

After getting in bed around 2 AM, I decided to do one more thing. It seemed pretty innocuous, but it would end up unravelling everything I had done. Remember me mentioning backing up with AptBackup way back during my prep work? I decided to go ahead run the AptBackup restore, so that it would load all of my jailbreak apps back on the phone for in the morning. Big mistake.

I have used AptBackup on a couple of occasions in the past, but evidently there are some issues with it in iOS 4 that I didn’t know about until it was too late. When my iPhone came back after the restore, the jailbreak apps were reloaded, just as expected. What wasn’t expected was that all of my App Store apps were gone….again. All of my work was down the drain for the SECOND time. I was torn whether to smash my phone into the wall, or break down into man-sobs. I was too tired, so I did neither and just went to sleep. Going into halftime, things don’t look good.

Jailbreak 24 – Me 10

The Day After- Trying to Pick Up the Pieces
My wife had been sick all weekend, and was actually feeling worse on Monday, so I ended up staying home and playing Mr Mom to my three kids. With a little bit of sleep and some time now on my hands, it was game on again. The first thing I did with the phone was plug it into iTunes and see what things looked like. My several gigabytes of app data was still there on my phone, but it had been shifted to the Other category. You know, the place were all of the jailbreak stuff that you install usually shows up. Since the data was there, I figured I would try and load all the apps back in and see if it would be consolidated. Oddly enough, my app data and settings still appeared untouched in each app, but that did not affect my huge Other category. Pretty soon, my 32 GB iPhone’s memory was maxed out, and it was clear that this attempt wasn’t going to work, either

After doing a little research, and discovering that some other people had experienced this issue with AptBackup, I tried to figure out what to do about my Other bottleneck. Unfortunately, the only solution I could find was to wipe out my phone and start all over again. I went ahead and did a backup as things stood, as the recommendations I read had suggested. From what I gathered, the Other data would be purged, and would not be restored to the device. However, the damage was already done. This is getting ugly now.

Jailbreak 31 – Me 10

The Restore- Round 2
After restoring the second time, I finally got into a groove. My iPhone’s settings were again, properly restored. All of my music and photos synced over without a problem. I then had to back and re-build my app screens in iTunes one last time. As I was doing this, syncing iTunes after each screen was rebuilt, I noticed how much smaller my App category was than before. I had a pretty good idea what that meant.

Evidently, the issue that the AptBackup restore caused corrupted or locked up all of my app data. That meant that this time, unlike the previous restore, my app data and settings were gone. This is why I said earlier that I should have just gone ahead and restored as a new phone. Other than my phone settings, I ended up doing all of that work and putting in a lot more time in the end. When it rains, it pours.

Jailbreak 34 – Me 10

Finally. SUCCESS!!!
The furious comeback begins. Thanks to my OCD backup habits, everything worked out in the end. My AppBackup files were put back on my phone as part of my iTunes restore, so as soon as I jailbroke my phone the second time and loaded AppBackup, I was in business. I quickly restored all of my game saves, app settings, and data. I then re-synced and restored all of my apps with their own backup methods. After all was said and done, I had about 99.9% of my original settings and data loaded on my phone. That’s not too shabby, considering all of the headaches along the way. While my furious comeback gets me back in it, it’s hard to claim a victory when your jailbreak takes over 8 hours.

Jailbreak 34 – Me 24

The Final Score
So, I came up a little short in the end, but it’s time to claim my moral victory thanks to the lessons I learned. I’ve always tended to follow my Dad’s motto- “When all else fails, read the instructions.” I usually get by just fine with that mentality, but this time, it came back and bit me pretty hard. In the end, all I really lost out on was time, but when you are married with three kids and have a job that doesn’t always fit in an 8-5 box, time is a luxury not to be wasted. Anyway, here are my recommendations after this little experience.

1. You cannot possibly spend too much time backing up before upgrading and/or jailbreaking an iOS device. No matter what else you do, this is the most important step. Be sure to include taking screenshots of your screen layouts in this step.

2. When upgrading a jailbroken iOS device, it is better to set it up as new. While this sucks, and is a lot of trouble, it is still true. My restoring from an existing backup is probably what caused all of my apps to disappear, even though the app data was preserved. If you can stand rebuilding your app screens, and are more careful than I was when putting your apps back in, maybe you can get away with a restore. However, for the smoothest experience, you should probably stick to starting over from scratch.

3. Past performance does not insure future success. We’ve heard financial companies state this in their commercials for years. It definitely applies here, too. Just because AptBackup worked for me in the past, I shouldn’t have blindly trusted it to work now after a couple of OS upgrades. A little follow-up research could have saved me a lot of time and struggle.

I did not get a chance to try AptBackup out again on my last restore. It might actually work fine if you upgrade, immediately jailbreak, and then run it before syncing any of your App Store data. However, after AptBackup almost doubled my time spent on this whole mess, I wasn’t in the mood to give it another shot. Hopefully, Cydia will eventually incorporate Rock’s app backup and restore features for jailbreak apps, but for now, you should just keep up with your jailbreak stuff on your own.

4. Take the time to Sync and Backup as you go. There were two different points where I was very close to being finished, only to have the house of cards crash in on me. When you get to that point of thinking, “I’ll just do one more thing….,” that is a great time to stop, do an iTunes sync, and backup. This could save you a lot of grief, especially if iTunes is properly recalling your synced apps and screen setups.

5. If you are a jailbreaker, you need to install AppBackup. This app saved me a lot of potential headaches and time on the back end of my job. If you are going to set up your iOS device as new, then it is absolutely essential. Best of all, it’s free. Just remember the caveats I mentioned about it earlier.

Jailbreaking can be a lot of trouble, but for those of us who depend on apps like MyWi, My3G, SBSettings, Lockinfo, Notify, or biteSMS, it is definitely worth it. Other than this one, my jailbreak experiences have actually been rather good, so I hope that no one gets the wrong idea or gets turned off from jailbreaking reading this article. I am still a fan and definitely recommend it those willing to try it. I know I will continue to jailbreak, myself, as one bad experience won’t dissuade me from giving it a go in the future. I will just take my lumps, learn from my loss, and move forward.

I just hope that, in writing this article about my losing effort against the formidable Jailbreak, I can help some of you avoid the roadblocks I ran into this time out. If any of you out there have had any of these or other issues while going up against Jailbreak yourself, we here at iSource would love to hear about it and learn from your experiences, as well. Please drop us a line in the Comments below, or here in the Forums to share your results- win, lose, or draw.



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  • Dave

    Great article fella.
    I have decided to keep at jailbreak 4.1 and not bother upgrading.
    Apart from being at the bleeding edge and having 4.2.1 i dont see what actual day-day advantages it offers me so I’ll stick with a stable iphone and save myself the hassle!

    You just saved another human.

  • Renkman

    Another_EPIC_review–good job! Thanks for the invaluable, well documented insight. I will go into my JB later tonight armed and dangerous.

  • jhrogersii

    Thanks guys. In retrospect, if you don’t have an Apple TV or a particular HP printer, then jailbreaking on 4.2.1 probably isn’t going to be a big deal. The main features you gain are AirPlay, which I think is cool but don’t really have a use for, and AirPrint, which is still crippled. 4.3 will be here soon, and I would hope an untethered jailbreak for it will come faster this time.

    Anyway, I’m glad my suffering will help someone. Good luck with your jailbreak, Rob.

  • Jay

    Excellent article! This would have served me well when I struggled with my jb on iOS 3.1.3

    I successfully used Greenpois0n to jb after upgrading to 4.1.2 – and didn’t restore as a new device! YIKES! I guess I got lucky!

  • Ricardo

    I don’t know if this would work on the phone but I just did the untethered jailbreak on my iPad. When i did the restore to 4.2.1 in iTunes, I unplugged it when it finished. I did not set up as new or restore from backup. I just went to Greenpois0n. After Greenpois0n did it’s thing, I connected to iTunes and restored from backup. I had no issues.

  • Erik

    I had the same 1013 error, when I tried to update my software from 4.1 to 4.2.1. It forced me to have to do a restore. So I restored, still same error. So I look into the error and find its the TinyUmbrella host file issue. So I change the host file, two times mind you because I forgot you have to run notepad as administrator to save the changes. Then I tried to restore again and it worked this time! I did restore from backup. Jailbreak went smooth, cydia installed fine. I chose to manually install all my packages in cydia as i usually do. Just made a list prior to all of this, then after my fresh jailbreak I installed them all manually. Didn’t take too long honestly. In the future I’m going to pass on Tinyumbrella for backing up shsh’s, I just use shshit in cydia for now.

  • Ron McCall

    Wish I had found this article before I spent the past weekend in much the same quandry as described here. I finally managed to un-brick my phone, using my son-in-law’s computer to complete the 4.2.1 upgrade, then re-jailbroke the phone. I had run PkgBackup, which stored everything in DropBox. However, doing a full restore from there did not go so well. I have been chasing gremlins for the past couple of days, and think I finally have the device functioning as I want it to. My worst problem: probably due to having installed Wi-Fi Sync on the iMac, which prevented it from validating the upgrade. Have since learned how easy it is to fix the iTunes Error: 1013.

    All in all, this description sounds much like my experience for my upgrade this past weekend.

  • jhrogersii

    Ricardo, I not exactly following you. When you do the upgrade from 4.x to 4.2.1, you have two options after the initial upgrade process is finished and your phone restarts. The first is to restore from a backup. This is the default option in iTunes after an upgrade. It automatically selects your most recent backup, and if you just hit next, that is actually what you are doing. You also have the choice to select a different backup file from a drop down menu if you have more than one.

    Second, you can set your iOS device up as new. You have to actually go in and select this. Unless I am mistaken, there isn’t another way to do an iOS upgrade.

    As for my experience, I am now wondering if it has to do with my long-running save file. I can’t tell you when the last time I set my device up as a new phone. I have never done it on my iPhone 4, and I honestly don’t remember doing it on my 3GS. I should probably do it the next time out, however. There are almost certainly artifacts left from several previous jailbreaks of different sorts hiding in that backup.

  • Solange

    I always restore as new, just to be on the safe side. I used Backboard, and didnt even have to set up my folders or app screens again, it put them all back in their place, it saved me a ton of time. Instead of using Appbackup to backup the data of some of my game apps, I just used Ifunbox to SSH in and backed up the folder of the app itself, and then after installing my apps in I just replaced the contents of the new folder with the old folder, and all my games were as they were.

    I bought Pkgbackup and used it to restore my Cydia repos and apps. It also claims to backup your pictures from Camera Roll, but that didnt work for me and I ended up losing my pics. But for just Cydia stuff, it was worth it.

    I really thought alot of just staying on 4.1, but I wanted to be able to use free Mobileme tracking, and not have problems with certain apps in the appstore telling me that I have to upgrade to 4.2 just to let me install. Im glad I upgraded to 4.2, I have mobileme, can install all apps with no problem, and all the cydia apps I use seem to be compatible. Im glad I made the jump….

  • iGnome

    Very useful article- after spending so much time on your jailbreak I think it’s great that you went the extra mile to write this so thank you very much.. When I went from 3.12 to 4.0 I restored from a back up and was pretty sure that my battery life took a big hit. So when I went from 4.0 to 4.1 I set up from new. The thing I found most irritating was all of my wifi networks that I no longer automatically connected to because I had lost the stored access passwords. Is there any way of finding the list of these and where they are stored and anyway of loading them all back in? Thanking you all in advance….

  • jhrogersii

    Thanks Solange. I almost mentioned Backboard in my article, but ended up deciding not to. I actually had it installed briefly, but removed it after I had issues with Winterboard crashing. I don’t do jailbreak themes, so I had no interest in trying to get it to work. Backboard requires Winterboard to be installed, so it went with it.

    I know I heard people complain the Winterboard caused crashes and severe issues, so I am still a little leary of it. How has your experience with it been, overall?

    Thanks for the iFunbox recommendation. I’ve heard of it before, but I have always just used WinSCP. However, while it works fine, it isn’t the most intuitive program in the world. I think I may just have to switch. I will just use it in conjunction with AppBackup, as it compresses its backup files.

    Thanks for the complement iGnome. I appreciate it. I am not sure where those files are stored on the device. If anyone else out there has an idea, feel free to let us all know. That would be a great thing to save out individually when setting up an iOS device as new.

  • Jdonner

    I’m an expert myself, working in the IT since ’87, but I have seriously doubts about your self-proclaimed “expertise” if you didn’t jailbreak a clean machine instead of one that was already jail-broken. Seriously, how could you’ve acted so noobish….sigh

  • Jdonner

    Just the history of Windows and its upgrades should have been a hint that things would probably not be a whole lot different with this iOS4 Iphone project.

  • Jdonner

    And what’s up with using Windows XP with its DLL hell and security issues anyway? “Expert” my ass….

  • jhrogersii

    Ah, a real “expert” in our midst. The next time I hear of someone looking for an IT guy that never makes a mistake or falls victim to their own arrogance, I will be sure to pass your name along. Unless, of course, the job also requires someone who can comprehend sarcasm and self-depricating humor.

  • Jim

    jhrogersii, you are the man. Jdonner, your life sounds upset.