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Previously, I had thought that it wouldn’t be necessary to jailbreak the iPhone 3G S. With over 50,000 apps in the App Store of which 30% are free for download, is there a need to jailbreak the 3G S? Surprisingly, the answer is still YES! A resounding one at that.

For the less initiated ones amongst us, jailbreak is a process in which you modify the system and OS of the phone, allowing you to install third-party applications not approved by Apple. For many reasons, some good – most bad, Apple doesn’t want you to install apps which have not been tested by them, or tested but doesn’t meet their standard and requirement. It is a good call, considering that the majority of the millions of us are not tech-savvy enough to solve mobile phone problems often due to a buggy software. What then, for the more tech-savvy ones amongst us? The answer: Jailbreak.

Jailbreaking has its risks too, and while some steps may look simple, the whole procedure is not for the faint-hearted. Many users have bricked their phones (i.e. rendered useless), sometimes necessitating a trip to a phone outlet to get it sorted for a fee. There are reports of permanent damage which required direct exchange, but I somehow think that in bricking a phone, the damage is never permanent and can usually be reversed, with due diligence during the procedure and in the research prior to that. Most dead phones happen because people get too impatient and jump right into doing it without having read or heard all the horror stories. I was soon to learn that myself.

I decided to jailbreak for many reasons. Despite knowing that it would void the one-year warranty on a three-day old phone, I went ahead with it. The push factors to that decision must have been compelling ones. And they certainly are. Partly, it was the ego. You see, all my phones in the past, regardless of platform and OS, had been hacked to a certain extent. If I had done it to Windows Mobile and Symbian OS, what good reasons do I have not to do it on the Mac OS X? Void warranty? Nope, not good enough.

These devices, being rich in multimedia features and equipped with state-of-the-art sensors have one main goal in mind. That is to serve their masters to the best of their bestowed abilities. How can they serve well if restrictions are put on them? If they had flawed mortal desires like we do, they would be begging to be hacked! Crashes and hangs? You know, sometimes we allow ourselves trivial pursuits which may be bad or unhealthy for us in the short run, but what is life if not for living? What is an iPhone if not for hacking? Jailbreak us, I hear them beckon.

To please my 3G S with its trivial pursuits, I decided to jailbreak it on the third day. If I know I was going to do it someday, let it be at the beginning of ownership. The earlier you do these things, the longer you get to reap its benefits and enjoy its full’er’-fledged features during its limited specs lifespan, expected of any technology and mobile device in the market.

For obvious reasons, I will not be going into the real reasons of jailbreaking a phone. Maybe in future posts this will be self-explanatory. But I will outline my procedures in the following, including where I went wrong, so that those of you treading the same path as I did may learn to avoid the pitfalls I had stepped into. I begin:

Performing a process like jailbreaking in the wee hours of the morning has its plus and minus. Plus is no one is around to disturb you, and you are unlikely to receive a call at that hour that would throw you off-track. Minus is, if you’re not used to being awake at those hours, you may lose concentration as sleepiness gets the better of you. For me, sleeping at 5 or 6 am is routine, so the lack of concentration out of sleepiness wasn’t so much the problem. The problem was knowing I had to sleep by 6 am, and not having enough time to complete the jailbreak process by then. In a bid to rush things, I had left out the part on “having done sufficient research”. I had read in a number of post that the purplera1n method was best suited for the 3G S. I had known about the redsn0w method as well, but that required downloading huge files. While that was downloading, I went ahead with the purplera1n method.

Plugging in the 3G S to the laptop, I initiated the purplera1n jailbreak, and in almost an instant, the screen on the 3G S went blank and at the same time, the program on the laptop crashed. I knew then something dreadful had happen. The iPhone with a blank screen that failed to respond to button presses and the purplera1n software that kept crashing on the laptop confirmed this. It was only then that I did further research and discovered that in much later forum and blog postings, the creator of purplera1n had claimed that his brainchild will only work with firmware 3.0 and not with firmware 3.0.1, due to some differences in the kernel and patches. And it was also then that I learned that redsn0w 0.8 was the way to go. What a time to realise that!

At that time, the firmware versions (3.0 and 3.0.1) needed for the redsn0w to work was being downloaded. At nearly 300 MB each, it didn’t seem I was going to complete the jailbreaking, if at all still possible, that morning itself. I did a bit of further research (which were to save me further trouble later as I had come to know) before I retired for the night. Or morning. Before going to bed, I removed the SIM card from the iPhone and inserted it into my old Nokia E90. It seems the E90 was going to serve me for the day to come.

The complete download was almost finish when I woke up 4 hours later, and was done when I was ready to go to work. I decided to do my jailbreak in the office.

With the firmware versions 3.0 and 3.0.1 in my hard disk, I thought I was already on safe ground. I plugged my iPhone and connected to iTunes on the laptop. iTunes came back saying that the iPhone was in recovery mode and needed to be restored. Fine. To point to the firmware sitting in the hard disk, you would need to click the Restore button in iTunes while holding down the Shift key (in Windows). After that, iTunes will then prompt you to select the file on the hard disk to be restored to the connected iPhone. After selecting 3.0.1, iTunes then went online to seek approval from the Apple server. The message came back saying the device was not eligible for 3.0.1. Somewhere along those lines. I repeated the procedure with 3.0 and received the same response. I believe that it was only possible if I did not hold the Shift button down and allowed iTunes to restore my iPhone to the latest firmware available then i.e. 3.1. Thanks to much research during the hours before bedtime earlier, I had learned that going to 3.1 was a point of no return that had left many woeful iPhone owners with regret and sorrow. If I had to, that would be the very last resort when I have exhausted all resources.

With the 3G S still in recovery mode, I started the redsn0w program and ran it like normal. I did this with the SIM card back in the iPhone. It may be a necessary step as advised by some forumers. When I came to the part to install Icy and Cydia, I made sure that ONLY the Cydia tick box was checked. I had also learned during the research some hours back that installing both Icy and Cydia would result in a lot of problems. Given Icy’s lack of support and hence implied unreliability, I chose Cydia. This is also recommended by many in the online community.

A few clicks on the subsequent Next buttons and I began to see some activity on the iPhone screen. When the picture of a half-bitten pineapple appeared on the iPhone screen, I knew that I was on the right track, and that the jailbreak process was on its way to completion. The only thing I wondered then was whether my phone with its firmware 3.0.1 and its contents would still be there once this was over.

It only took about a minute or so after that before that familiar “slide to unlock” appeared on the screen, together with my selected pebbles wallpaper. I knew then that all was fine. Everything had been left as it was and the phone was finally restored, with Cydia sitting on the springboard. Excellent. Keeping the E90 back in the laptop bag, I was on my way with the iPhone once again.

For those of you with an unlocked iPhone 3G S running on the firmware 3.0.1, this would be the surest way to go. If your iPhone is a locked version, of an earlier model or with a firmware other than 3.0.1, a different method and further research would be needed.

The detailed step-by-step for the redsn0w 0.8 method outlined above can be found here.

Good luck!