This essay examines the relationship of philosophical pragmatism to the practice of reflection in service-learning. Service-learning theory and practice often elides over or ignores entirely the principles of inquiry as developed by Dewey. The exercise of reflective thought requires that educators create a situation of discomfort for learners, and mandates that students examine the warrants of settled belief (i.e., assumptions). A brief historical overview of the major strains of American pragmatism is presented, followed by a summative review of important treatments of reflection in service-learning. The elements of inquiry in Dewey are then analyzed and their implications for service-learning considered.