Diplomatic practitioners and policy makers represent an important, although frequently neglected, resource for teaching about international relations. The insights and stories provided by practitioners regarding key processes and events are often able to inspire our students to engage complex material and to play a much more active role in their own learning. While it is possible to argue that any type of practitioner contact is beneficial in terms of going beyond the material covered in textbooks, there are definite challenges associated with how to most effectively integrate these experiences with overall student learning. What type of format is most conducive to providing students with an insider's view? What type of preparation is required before contact with practitioners? How can student learning be evaluated in terms of assignments and debriefing activities? And finally, are traditional student feedback mechanisms appropriate for a course that involves a substantial practitioner component? This article investigates each of these challenges in the course of discussing one mechanism for bringing practitioner experience into the classroom, the United Nations Intensive Summer Study Program.