iPod Jailbreaking for Unix Geeks

As an employee of an academic institution, a new Macintosh this summer comes with an iPod. Who could resist an iPod Touch? And who can resist the urge to jailbreak it?

Not me.

1. So what's jailbreaking anyway?
   Jailbreaking is the process of installing a new package manager onto your iPod. Apple's App Store is the first package manager. redsn0w installs Cydia, which is a graphical front end to APT. With Cydia installed, you have access to a number of different package repositories from which you can install software.
2. Why can't I just install software?
   Remember Trusted Computing? Your iPod is running something like that and will only execute signed code. Jailbreaking modifies your iPod's firmware so that unsigned code (like that installed via Cyida) will execute.
3. Why is this so hard?
   It isn't. redsn0w is point and click. The hardest part is holding down the iPod's home and power buttons simultaneously and redsn0w even has little countdown timers so you get the right sequence.
4. How well does it work?
   Surprisingly well. Underneath this cryptographically-protected shell is OS X, and, as a Unix implementation, it takes a lot of abuse and keeps on working.
   
5. Why would I do this? Isn't being able to ssh into a shiny little slab in your pocket a good enough reason?