For over 11 years the final two iPod nano models somehow managed to evade the best efforts of even the most tenacious hackers to subvert - something which I took personally. The first public jailbreak of an Apple device was a prize simply too enticing to ignore. In this talk I'll explain how I went from zero access to full, persistent and unobstructed control over the entire device. Join me on this tale of ancient font formats and blindly trying to leak bits out of the darkness....