To date, the application of quantitative security and privacy metrics metrics has seen its greatest successes when exploring the worst-case properties of a system. That is, given a powerful adversary, to what extent does the system preserve some relevant set of properties? While such analyses allow experts to build systems that are resistant to strong attackers, many deployed systems were not designed in this manner. In fact, there is growing evidence that users' privacy is routinely compromised as a byproduct of using social, participatory, and distributed applications.