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This qualitative comparative case study examines school- and community-level factors that impact community involvement policy and its implementation. Eighty-one 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 community involvement quantity and quality in the two districts yielded insights into collaborative processes. A district-level liaison was essential for connecting community organizations with educators in schools. School leaders played key roles in determining whether community involvement would take place in schools, and what form it would take. The research identifies leadership roles in community involvement policy and practice, and the structures and cultures that facilitate it.