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This study analyzes how Chicago Public Schools high schools interpreted and enacted the district’s Whole School Safety (WSS) initiative—a policy reform aimed at increasing physical safety, emotional safety, and relational trust within schools. Using qualitative content analysis of 53 school-authored safety plans, we explore the strategies schools proposed and the challenges they faced in translating equity-focused policy into practice. Findings highlight common tensions—between relational goals and control-based infrastructure, between community voice and procedural mandates—and reveal capacity gaps in implementation planning. For school and district leaders, the study offers insight into how local planning processes both reflect and constrain broader efforts toward justice-oriented safety reform. It underscores the importance of coherent supports, inclusive engagement, and structural alignment in leading community-responsive change.