This paper reports on an investigation of the educational value of a second run of an international conflict resolution role-playing exercise. While the use of simulations and games in the classroom appears to be on the upswing, a second run of the same exercise seems to be a pedagogic tool that is rarely employed. One reason for this may be that having played out a scenario once, there is often little interest on the part of students to play it out a second time. By designing an iterative series of exercises, however, one can hope to make a second run just as valuable educationally than the first. This approach borrows from the realm of governmental policy gaming, where an exercise is set up as a series of discrete moves, each of which requires the participants to assess the situation and elaborate policy choices. In each successive move, new information or an intensification of the crisis, injected by the game controllers, forces the participants to reformulate their policy. By designing an educational game along analogous lines, the instructor can offer students successive scenarios that are sufficiently different to engage student interest, but basically repeat the same substantive questions for resolution – effectively giving the students a second bite at the apple and allowing them to demonstrate a progression in learning. To test this approach, the author designed a role-playing exercise addressing the role of the United Nations in resolving international disputes. By constructing an exercise modeled on African crises brought to the UNSC, in this case encompassing terrorism, the rights of ethnic minorities, cross-border military clashes and competition for energy resources, while raising humanitarian concerns and questions of sovereignty, students were given the opportunity to make those types of decisions for themselves. A further iteration of the scenario, administered a few weeks later, allowed students a second chance to address the same questions based on additional developments that showed the original issues underlying the crisis had remained unresolved.After each session, the students were surveyed on the motivations for their actions during the game, their views on the UN's role in crisis management, their readiness to see the UN address specific types of issues, and their assessment of the UN's effectiveness. The outcome of the surveys conformed to the hope that the simulation design would enhance, rather than diminish, the value of the second run of the scenario. Student assessment of each run of the simulation was highly positive, but even more positive for the second run. The surveys showed definitive and nuanced changes in their attitudes and behavior from the first to the second run. The students felt better prepared and their motivation for action changed in ways indicating greater immersion in the game environment, a greater focus on the appropriate issues for UN engagement, and a correspondingly lesser display of a game mentality. Perhaps most tellingly, none of the students found the second run superfluous and only 12% thought they had gained more knowledge from the first run. Nor was there any sign of boredom. While the verdict was unanimous (100%) that each run had been worth doing, over 80% thought the second run was more fun.