In this article, we interpreted, in light of Mezirow's theory of transformative learning, interviews with 13 educators regarding their work with marginalized adult learners in prisons in the northeastern United States. Transformative learning may have been aided by the educators' response to unplanned activating events, humor, and respect, and being a role model, and counselor. Teachers presented activating events that they perceived as supporting resistant learners in altering their meaning schemes and revising their frames of reference. Administrators of educational programs for marginalized adult learners can help prison educators develop these pedagogical practices. Practitioners and researchers may wish to explore humor in restricted learning environments as well as the challenge mandatory prison classrooms present for the field of formal adult learning and transformative learning theory.