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This qualitative comparative case study examines school- and community-level factors that impact community involvement policy and its implementation. Sixty-two participants (directors of education, superintendents, administrators, teachers, parents, community members) from two districts in the same southern Ontario region participated in individual open-ended, 45-minute interviews. Observations were conducted, and documents were collected. Differences in quantity and quality of community involvement in the two districts yielded insights into collaborative processes. District-level leadership was needed to clarify policies and processes, and to connect community organizations with educators in schools. Potential partners’ needs and goals were essential considerations. Findings extend research by identifying administrators’, educators’ and community members’ leadership roles in community involvement policy and practice, and the structures and cultures that facilitate it.