Tor. PGP. OTR. We have privacy enhancing technologies (PETs), but when was the last time you used privacy software that “just worked’’? Just like security cannot be an afterthought bolted on after the software is written, neither can usability. In this talk, we will discuss why usable PETs are important, why creating usable PETs is challenging, and conclude by describing a real usability evaluation of the Tor Browser Bundle, with a focus on how hackers can perform practical usability evaluations of their own, using tools from the fields of experimental psychology and behavioral economics.