The iPad is hailed by Apple to be a "Magical and revolutionary" device. Whether or not that is true is a fact in heavy debate. Personally, I don't think so. But it IS a very interesting platform for penetration testing.
With the release of the Spirit userland Jailbreak, the iPad is now a more versatile platform for development and research. Using the Cydia APT repository system (which uses Debian-style APT packages ported specifically to the iPhone OS), it is now possible to install packages which vastly increase the extensibility of the iPad. Already there are multiple security applications ported to the iPhone OS platform, and with the addition of the Gnu compiler and kernel headers, it is possible to natively compile even more.Pentesting on iDevices is nothing new. Thomas Wilhelm (aka Hacker Junkie) gave a talk at Defcon 17 about using the iPod Touch as a pentesting platform. We'll attempt to look at expanding upon his work and applying it toward the iPad.