The intensive group process inherent in alternative break service trips offers a unique opportunity to foster transformative learning in undergraduate students. This exploratory study focuses on a two-year project in which graduate students who were professionally educated in group work led undergraduate students in national and international service trips focused on working with the poor. Analysis of triangulated data suggests a significant change in attitudes toward the poor during the service trip. This shift appears to be facilitated through the group process guided by the graduate student group leaders. Specific strategies that promote group development and reflective group interaction are identified. Areas for additional study are suggested.