The classroom teacher plays a pivotal role in any formal educational environment. More specifically, how this individual is involved and how s/he structures activities and discussions about a topic depends on the preferred learning style, personal demeanor, and educational philosophy of the teacher. For teachers that employ service-learning pedagogy in their courses, these expectations and factors do not vary. Teachers motivate students, help them to make meaning of experiences, and assist them in making connections for future action. These roles become complicated, however, when novice teachers do not have sufficient pedagogical training and/or are not given ongoing guidance by administrators. Using data from interviews with students and administrators at an urban Catholic high school, the qualifications and roles of the service-learning teachers, and their intended roles as described by administrators, are compared to the perceived roles as voiced by students. Implications and recommendations are discussed with specific attention to administrator communication, types and frequency of reflection activities, and, as a result, tensions of service-based models of experiential education in Catholic schools vis-à-vis the development of social justice.