This article investigates the use of photography as a narrative approach to learning in the context of postsecondary education. Two cases are presented: a social studies methods course in a teacher education program in the South of the United States; and a senior undergraduate seminar on global violence at a university in southern Ontario, Canada. With each case presentation we explore how the assignment of photography both instantiates and cultivates the student's ability to tolerate, represent, and interpret encounters with pedagogical complexity. A term of learning that apprehends the pedagogical encounter as made from the tensions between knowing and uncertainty, pedagogical complexity is discussed with regard to the psychoanalytic concept of containment. Using a case presentation approach, the authors explore the possibilities and limits of the assignment of photography in relation to the pedagogical work of containment. Engaging a cross-case analysis of the research data, the authors conclude by discussing the potential for photographic practices to contain the dynamics of pedagogical complexity.