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This qualitative comparative case study examines factors that enable or limit school-community collaborative activities’ implementation. Eighty 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. Limited time, money and distance between collaborators challenged partnering. Partnership flexibility and feedback provision ensured partnerships met participants’ needs. Common goals, shared beliefs and values, and district and school leaders’ promotion of a welcoming environment for collaborators encouraged partnering. Valuing others’ contributions, and building reputations for successful partnerships enabled partnering and promoted future collaboration. Findings extend research by identifying factors that facilitate or frustrate administrators’, educators’ and community members’ efforts to collaborate.