As communication in both formal education and workplaces is more and more mediated by online content managements systems, it is possible to simulate online within professional education the systems of genres that characterize professional work. This paper reports on a research group that has been designing, teaching with, and researching online, multimedia, fictional case studies for professional education, which dynamically represent the genre systems and communicative practices of organizations. The theoretical underpinnings of the simulation and the pedagogy lie in a New Rhetoric or activity approach to genre. A qualitative analysis of students’ responses suggests that this approach may successfully address problem of the lack of transfer of genre knowledge from formal schooling to professional work.