During revolutions, strategic interactions among civilian policy makers, armed forces, and opposition groups shape political outcomes—most important, whether a regime stands or falls. Students from advanced industrial democracies frequently find these dynamics counterintuitive, even after completing readings and engaging in traditional instruction methods. We therefore sought to improve pedagogical outcomes by designing a simulation based on scenarios similar to those witnessed during the Arab Spring and Ukraine’s Euromaidan Revolution. We divided students into four teams representing the regime, the armed forces, and two distinct groups of anti-regime dissidents. Rules were designed to incorporate the best recent scholarship on each category of actors’ behavior, such as the probability of military units defecting to protesters and the ability of riot police to repress urban uprisings. By forcing student teams to make decisions under time pressure, we obliged them to wrestle with the uncertainties and fears of betrayal inherent in complex civil–military emergencies.