This study extended research on transformational service learning by examining the impact that a community placement context can have on college students' transformational processes. Kiely's "Transformational Service-Learning Process Model" was used as a framework to better understand how context, dissonance, and student reactions are interrelated. Using the consensual qualitative research method of qualitative analysis, we examined 43 essays written by students in a service-learning course that focused on the development and maintenance of poverty in the United States. The essays described an experience the students found to be "eye-opening." Our findings suggest that context of the community placement (i.e., job responsibilities and service location) shapes the types of disorienting dilemmas students identify and the reactions they report; working inside (e.g., shelter) and outside of a community placement may produce different transformational paths. These findings have implications for educators and researchers and highlight several different potential pathways of transformation within Kiely's general framework.