Every year, RVAsec hosts an after-party to close out the first day of talks at the conference. For the last two years, that nightly entertainment has been CASINO NIGHT, an opportunity to bet fake money on games of chance in order to win some very real prizes. Unfortunately, through some fault of my own, Casino Night will not be returning this year. Join me for a retrospective of the last two Casino Nights: what went right, what went wrong, how systems (and people) can be gamed, how to adapt to new information, how I managed to win numerous prizes, and more. We will discuss how to harness game theory, social engineering, statistics, and other things that will get you kicked out of a normal casino.