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The goal of this qualitative case study of one urban middle school was to investigate and portray teachers’ beliefs about the dilemmas they faced as they implemented service-learning in their classrooms and how they managed these dilemmas within their specific school context. Through an analysis of interview, observation, and document data gathered over a five-month period, three broad dilemmas emerged: needs of the server vs. needs of the served, traditional vs. experiential education, and teacher control vs. student independence. These dilemmas arose as teachers at the middle school attempted to reconcile the expectations of a variety of educational stakeholders, including parents, administrators, and state and local school boards, the needs of those at the service sites, and their own beliefs about teachers, teaching, and students. Using the language of dilemmas which allows for a consideration of “the macro in the micro” it became clear that the dilemmas identified existed partially because of a pervasive teacher culture that hinders work among teachers at a school and between teachers and individuals at service sites. Also, issues of school reform sustainability are inextricably linked to service-learning, both because service-learning is a reform itself, and because service-learning is impacted by other reforms, such as the move toward standardization of curriculum and assessment.

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