The rapid acceleration of online course offerings presents a design challenge for instructors who want to take materials developed for face-to-face settings and adapt them for asynchronous online usage. Broadcast lectures are relatively easy to transfer, but adapting content is harder when classes use small-group discussions, as in role-playing or negotiation games. To be successful, such environments should address three interrelated design challenges: (a) sustaining engagement, (b) promoting content-focused discussion, and (c) promoting reflection-on-action. This article is a case study of how one interactive role-playing game, Island Telecom, was adapted for online play. We describe eight design features, including automated player roles and a structured team decision-making process, and show how they match with design challenges. Feedback from a recent run of this game shows that, although students still prefer to play face-to-face, they now also give favorable ratings to the online version. Feedback on specific adaptations is also presented.