The central purpose of this article is to explore research, issues, and perspectives on the implementation of service learning programs to improve student achievement in at-risk student populations. The implementation of service learning programs takes place within multiple contexts and across several terrains. The complexities of implementing service learning are captured in a framework of "contextual dynamism" which consists of six interrelated terrains: the political, the economic, the accountability, the financial, the demographic, and the staffing. In this article, the authors explore each of the terrains, ending with recommendations for policymakers and practitioners.