I’m going to get this topic out of the way early on, as it is a topic that is taboo in many circles, but important, none the less. I am not going to explain here how to Jailbreak your iPhone/iPod Touch–a Google search can lead you where you need to go for those details. I am going to explain what Jailbreaking is, the reasons behind Jailbreaking, some cautions, why I Jailbroke my iPod Touch, and what you can do with a Jailbroken iPod Touch. So read on to see my experience with Jailbreaking my iPod Touch…

“Jailbreaking” is a method of hacking your iPhone/iPod Touch such that you can install and run third-party applications. It is typically done by taking advantage of one of several vulnerabilities in the iPod Touch’s software. These vulnerabilities, could conceivably be used to spread malicious code such as trojans and viruses, but in this case, it has one intention: install a small, yet powerfull application called Installer.app. Once installed and launched, Installer.app provides several important functions: Connect to one of many user-definable application repositories to select, download, and install those applications; manage updates; uninstall applications; and to manage the sources of those repositories. It’s currently at version 3 and is a very solid and well-developed application.

One of the original (and for many, current) intentions of Jailbreaking was to be able to unlock your iPhone so the user could use a different SIM card, thus “freeing” you from AT&T. I’m not going to address the legal ramifications of this, but suffice it to say, a huge side effect of a Jailbroken iPhone was that you could install and run other applications as well. Thus the Installer.app was born. Obviously, the iPod Touch does not have phone capabilities, so the only reason to Jailbreak an iPod Touch is to provide the ability to run additional applications. And it is proving to be a very useful feature.

As a word of caution, it is important to understand that Jailbreaking your iPhone/iPod Touch is not supported by Apple. Any applications you install are considered “unauthorized” because they are not digitally signed or distributed by Apple. It is obvious that one of Apple’s design goals is to provide a product that requires as little support as possible. By Apple controlling what gets installed, the likelihood of support issues goes way down. When you let the user install whatever applications come along, you raise the potential for support issues. In fact, there have actually been a couple instances of malware that slipped into the applications available to Jailbroken devices to which Apple promptly says, “I told you so.”

Further, some methods of Jailbreaking, if not followed precisely, can leave your iPhone/iPod Touch in a “bricked” state turning it into a sleek-looking multi-hundered dollar paperwight. And some people have either had problems with the Jailbreaking process, or simply don’t understand the process resulting in a messed up device. The bottom line here is that as an iPhone/iPod Touch owner, you really have two choices: Follow Apple’s upgrade and support path, or venture out on your own into the world of jailbreaking. (One point of note is that currently, in almost all cases, simply doing a simple “restore” through iTunes will bring your Jailbroken iPod Touch back to a “stock, non-jailbroken state.)

So once you have Jailbroken yout iPod Touch, what can you do? Well, launching the Installer.app application reveals a modest list of available applications. One of the categories is called “Sources” which, if installed, add yet more application repositories, expanding your list of available applications. And all of these applications are true, honest-to-goodness applications ranging from very simple to amazingly sophistocated. From eBook readers to games to UI enhancements, the list is vast. And yes, you can even install Apache, turning your iPod Touch into a full-blown Web server!

So why did I Jailbreak my iPod Touch? Installation of third-party applications is obvious, but it went deeper. My original goal was to try out the various applications that were being developed to get a feel for the true capabilities of the iPod Touch. Folks, the results really were amazing. Many of the applications I played around with showed off what the iPod Touch can do, and many were amazingly professional. If the skill and imagination of the authors of Jailbroken applications is any indication of what is to come once Apples releases it’s forthcoming Software Development Kit (more on tha later) we have lots of exciting times ahead of us!

I’m currently running firmware v1.1.3, and I purchased the “January Update” applications (more on that later.) After jailbreaking, I have installed a nice suite of applications, utilities, and tools that have transformed my iPod Touch from an advanced media player to a powerful entertainment and information resource. Here is an example of what I have installed and use regularly:

advanced calculator
eBook reader with the full text of the KJV Bible, many of the U.S. Founding documents, several works of Shakespeare and Edgar Allen Poe, the five books of the Hitchikers Guide to the Galaxy trilogy, and a number of other eBooks
Dictionary containing one of Miriam Webster’s dictionaries
Sketch Pad to jot hand-drawn notes
Wiki2Touch, an amazing offline Wikipedia application providing the entire text content of Wikipedia–offline
And a few games

Here are some screenshots of several of the applications:

And all this leaves me well over 4GB of space to load up my favorite photos, songs, and a few videos.

I have high hopes for Apple’s direction in releasing their SDK, and I hope that even a small portion of what I’ve seen on my Jailbroken iPod Touch is “officially” made available. But until then, I’m enjoying the vast resources in my pocket.