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Community Schools are a place-based reform strategy that attempts to improve educational and neighborhood outcomes. Aiming to galvanize broad-based community partnerships and push back on top-down, high-stakes accountability systems, community schools take an integrated approach to achieve school reform linked with community development. As such, the purpose of this study is to examine the out-of-school challenges of implementing a community school reform strategy in a Midwestern city in the U.S. and the opportunities for educational leadership programs to prepare school leaders to confront these challenges. This study addresses two research questions: (a) what out-of-school challenges emerge during the implementation of a community school reform strategy in a low-income, racially diverse community? (b) how might educational leadership preparation programs prepare leaders to respond to these out-of-school challenges? Utilizing case study methodology, we employed interviews, observations, document sources, and field notes to collect data. Critical urban theory is used as a conceptual lens. Findings suggest three out-of-school challenges emerge when implementing a community school strategy: the corrosive impacts of school desegregation policies, neighborhood school closures, and fiscal poverty exacerbated by deindustrialization. Finally, we explore how educational leadership programs can prepare leaders to address these out-of-school challenges through anti-racist and community-based leadership practices.