[digg-me]… that seems to be the question. And no, to your dismay I may not have the answer. But I have put together this small guide that will hopefully help you find the answer on your path to iPhone glory and satisfaction.

Let’s start by discussing some reasons against jailbreaking, just so you’re not, not doing it for the wrong reason, make sense? Good, here we go.

It’s illegal.

Well, it is illegal. By jailbreaking your iPhone, you are actually infringing Apple‘s Copyrights on the iPhone firmware. Although the iPhone is yours, you are legally not supposed to touch any of the software. Besides, by installing non-Apple-approved software, you are violating both Apple and AT&T‘s TOS (Terms Of Service). The reality is, it’s about as “illegal” as downloading music off of Lime Wire or Bear share, which means the chances are greater for a snow storm in July, in Jamaica, than you getting caught, even further more in any kind of legal trouble for jailbreaking your iPhone.

What about messing my phone up or ‘bricking’ it?

It is in my experience that ‘bricking’ the iPhone is a term of the past. Used only in preliminary jailbreaking days when all of this territory was new and unexplored. I myself have seen several errors, an all black screen, an all white screen, and a busy icon for half an hour while trying to jailbreak my phone. I believe a quick restore either through iTunes or the holding down home+power reset process on the phone will take care of many problems you may incur.

Hacking an iPhone sounds complicated, I’m not that computer savvy.

Surely this one is up for debate. But I think most of us will agree that the process has become fairly simple. In fact, the premier jailbreaking program out right now QuickPwn (how to use QuickPwn guide here), has an easy to use GUI (graphical user interface), and takes literally 5 minutes. Leaps and bounds above the old command line hacking days. Completing this process not only opens up to free “App Stores” (Cydia and installer 4.0), but also can turn your phone into an easy to use portable hard drive, and give you the ability to install “cracked” apps. Cracked apps are applications in the Apple App Store that people have cracked and made available for download for free online.

Depending on your firmware of your iPhone (on your iPhone, go to ‘settings’, then ‘general’, and finally ‘about’, your firmware is listed next to ‘version’), you can Google the words “jailbreak my iPhone”, and find 1000’s of hits and tons of guides on how to do it. Maybe even try including your firmware in your google search to help narrow it down.

If the list above didn’t extinguish your fears of jailbreaking, then maybe it isn’t right for you. However, I love it, so if the features I use on my jailbroken phone listed below sound cool, you might lean toward the ‘to jailbreak’ scenario.

  • I can share files, information, and media between my phone without connecting any chords
  • I have hidden files, notes, and folders that you can only access from my laptop
  • I can try out any application I want for free, before I spend money at the Apple App Store (comes in handy for programs like Jaddu that are $24.99)
  • I can install 3rd party applications from Cydia and Installer (free) that aren’t available anywhere else
  • My $400.00 iPhone, now feels, like its worth $400.00

So to Jailbreak or not to Jailbreak can be answered with these little tips.

Jailbreak if:

  • You want to explore more options with your iPhone
  • You want to try some applications before you pay those hefty price tags
  • You want more games and cool software

Don’t Jailbreak if:

  • Your completely computer illiterate
  • Just think it’s cool your iPhone is a touch screen phone.