Many online courses fail to promote the active construction of student knowledge or camaraderie among student peers. Accordingly, online course designers and instructors are challenged to promote purposeful peer student dialogue and establish a sense of belonging where all learners perceive themselves as stakeholders in the course community. Online role playing is not a common activity, and electronically networked jigsaw role plays appear to be rarer still. In this article, we describe the transition of a face-to-face jigsaw role-play exercise to a primarily asynchronous graduate-level online course in education. Data collected from various sources suggest that students enjoyed online role play and valued it as a learning experience. We conclude with reflections, lessons learned, and future plans as we continue to explore the challenges and benefits of online role-play in graduate level online courses that serve adult professionals.