Back in the early days of iPhone jailbreaking, things weren’t exactly easy. Jailbreaking my first generation iPhone took the better part of a few hours, running command line scripts and ensuring that you had the correct files for your particular baseboard or flavor of OS.

I’m happy to say that this time around, it’s a whole lot easier!

First off, jailbreaking, not to be confused with unlocking, is the process of breaking the chain of trust within the iPhone, giving it the ability to run unsigned and unapproved apps. While jailbroken phones are often unlocked as well, allowing them to function on any GSM carrier (not just AT&T), one does not need to unlock the phone to take advantage of a plethora of useful apps.

Jailbreaking the iPhone via Pwnage Tool will not only give it the ability to run unsigned apps, but will also install the Cydia package management system (think unofficial App Store, if you will). You can the install and/or uninstall tons of apps, extensions and add-ons to your iPhone directly over the air.

Step 1: Back-up Your iPhone

This seems rather self-explanatory, but it’s best to back up your content and media before attempting a jailbreak. This takes on an extra level of importance due to the fact that we will have to add the content back to the phone once we have jailbroken it– and it’s always best to work from a recent back-up to ensure you aren’t missing any recently added content.

Step 2: Download Pwnage Tool

The iPhone Dev Team has long been known for tackling each new firmware revision and developing a handy tool to facilitate both jailbreaks and unlocks. An international collection of developers and hackers, the Dev Team maintains an updated blog with troubleshooting information, FAQs and news about upcoming changes to the iPhone firmware. If you are interested in unlocking/jailbreaking iPhones, it’s definitely your one-stop shop.

To put this question to rest early, Pwnage Tool is only available for Mac. So if you’re a Windows user and you don’t know a Mac owner, this would be a great time to make a new friend.

Unofficial download mirrors:

Once downloaded, you can run Pwnage Tool and you should be presented with a screen similar to the one pictured. You should note that Pwnage Tool offers you a few different modes to choose from, depending on your level of comfort or desire to customize. That said, about 85% of users are probably going to want to opt for “Simple Mode” as it will ask you a series of simple questions to expedite the configuration of the jailbreak.

It’s important to note that Pwnage Tool will jailbreak and/or unlock phones. So if you need your iPhone to work on say, T-Mobile, make sure you answer “No” when the tool asks if your phone “would activate normally”. Once you have answered the prompts from Pwnage Tool, it should begin to create a custom installer file (IPSW) file that will replace your existing iPhone OS. In the event that Pwnage Tool cannot locate the previous version(s) of the iPhone OS (which are traditionally stored on your computer), it may prompt you to supply one. In this rare case, search Google for the most recent IPSW, noting the version number in your search.

Step 3: Apply The Custom Install File Via iTunes

When Pwnage Tool has finished performing its magic, your iPhone has yet to be changed. In order to apply the custom IPSW we built using Pwnage Tool, we must now restore from iTunes.

Pwnage Tool should have placed your phone into recovery mode (see image). In the event that Pwnage Tool does not launch recovery mode on your phone, or you faced an error and had to turn back, follow these directions to activate recovery mode.

With the iPhone in recovery mode, connecting it to iTunes should yield this message.

While the iPhone is connected, you should see a button for “Restore”. Option-click “Restore” (Shift-click on Windows). This should provide you with a file selection box which allows you to select which firmware you would like to load on to the device. Select the custom firmware bundle we created via Pwnage Tool, which more than likely resides on your desktop.

Once iTunes has installed the custom IPSW, you should note that your music, videos, apps and accounts are have been removed from the phone– no worries. Simply restore from your last back-up. It may take up to 20 minutes depending on the amount and size of the media you are transferring back to the phone.

After your phone’s media has been restored and the restart has completed, simply find the newly-installed Cydia app and start downloading unapproved apps!

That’s it! Happy jailbreaking!