This article presents an approach to improve urban resilience by examining crisis dynamics through a role-playing game. The set of exploratory exercises extend the Archaria 2035 scenario and geographic information system model, which was developed by the North Atlantic Treaty Organization (NATO) to advance concepts that support military operations. Participants (graduate students) worked in teams to identify and map critical relationships related to health, safety and welfare through a modified version of the Political, Military, Economic, Social, Infrastructure, Information (PMESII) framework. Next, each participant was given a one-page stakeholder profile that specified motives, kinds and degrees of influence, and connections to other stakeholders. This information was used to create maps that showed how each character understood the city. Crisis event details were revealed a day-and-a-half before the game. NATO staff contributed to the event by presenting courses of action to restore security and order. Participants gave opinions on how their characters might act during the event and react to the proposed military operations. Conversations created temporary collaborations among some stakeholders but also conflicts among others that could create additional problems. A post-game assignment asked participants to write memos on specific policies and plans that would reduce vulnerability to the crisis. As a matter of pedagogy, results the demonstrate the value of role-playing to consider multiple perspectives and second- and third-order effects of a crisis. Specifically, connecting gameplay conversations and results back to initial ideas about health, safety and welfare contributed to reconsiderations of assumptions about contingent relationships.