There have been countless efforts to improve academic achievement in public schools across the United States, especially in urban school districts. Few efforts, however, use rigorous analytic modeling tools to anticipate and prevent the potential side effects of change. This chapter proposes the application of system dynamics on educational reform efforts by offering a conceptual model, literature review, and research agenda to identify and mitigate the potential side effects of reform. The model is based on interviews and workshops with public school leaders, teachers, and parents in a midsized midwestern urban city. We identify a "capability trap" that may lead to policy resistance with educational reforms. Limitations to this approach are noted, and future areas of research are identified.