This article chronicles the coordination and better integration of existing institutional resources to support "cocurricular" themes embedded in the provision of a large enrollment, video-mediated undergraduate operations management (OM) course. The name Project Cheddarfield refers to a 2008 initiative in which two professors team-taught an OM course to over 600 undergraduates on two different continents through the repeated rapid exchange of digital video between the United States and Singapore. Simultaneously infused in this core curricular delivery were themes of global awareness and study-abroad, including the promotion of one particular opportunity that bridged the two campuses. This action research narrative spans over 5 years of related activity leading up to the initiative, as this project is best understood as a "trajectory," or the evolving result of design adapting to unfolding realities.