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This paper looks at strengthening parent engagement in education, focusing on leadership strategies for reaching and supporting parents. The qualitative case study of a district’s multiple approaches for enhancing parent engagement involved 8 individual and focus group interviews, observations, and document analyses. The superintendent and principals shared leadership with school councils for developing initiatives. They collaborated with community organizations to provide parenting support, social services and resources to enable participation. Despite some success, the leaders were challenged to establish engagement programs widely across the district due to a managed, hierarchical, organizational structure and limited parent input on educational goals. The research contributes to a discussion of enhancing relations among families and schools to promote all students’ academic achievement and wellbeing.