Creating positive learning outcomes regarding terrorism can be challenging. The nature of the topic offers several obstacles to learner understanding, not least of which is how to enable students to transcend their own cultural perspectives and develop deeper and more objective insights regarding the groups and causes that foster terrorism. Following an exploration of the growth in terrorism as an academic subject and the challenges posed to teaching in this area, this chapter presents a possible solution by describing an online role play exercise that has proven learning results over more than 25 years of usage. This tool, grounded in an experiential learning approach, can assist in easing some of the stresses faced by teachers and institutions, while also offering deeper and more insightful discoveries for participants.