Building on a vision of popular education originating from Paulo Freire’s teaching in Brazil, critical pedagogy is a radical approach to adult learning that brings dialogue and social action into our teaching spaces. Historically, popular education programs based on critical pedagogy have been attractive to learners coming to education via non-traditional pathways. The approach acknowledges and celebrates the life experiences of all learners and, because learning is connected to social justice in the real world, activities are relevant and authentic by design. In this chapter, we examine the ways in which key aspects of critical pedagogy (for example, empowering students, dialogue in class, drawing on students’ capabilities and experiences, problem-based learning) played out in an international relations course taught on a traditional university campus and in a Clemente program. Differences in course outcomes from the two teaching environments are described. While the student cohorts brought different experiences to the courses that changed group dynamics, some benefits of the pedagogical approach were gained by all learners.