In this essay, author Steven Ciampaglia reflects on the creation of a guerilla art course he and a colleague designed to engage students in the process of creating contemporary art relevant to them outside the traditional classroom setting. He examines how reflecting on his teaching practices led him to rethink the key objectives and design features of the course. Ciampaglia chronicles his experiences working with students as they wrestled with the various challenges involved in conceptualizing and executing a collaborative guerilla art project. He reflects on the ways in which his own assumptions and teaching practices interacted with the interests and efforts of the students to produce a successful and replicable teaching model.