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Several decades of research has generated a near-consensus on the link between positive student outcomes and effective engagement between educators and families. Despite the widespread acknowledgement of this connection, many educators continue to struggle to engage families in ways that are both culturally responsive and sensitive to power dynamics. Though barriers to family engagement have been explored in depth, little research exists about what family engagement looks like in schools with above-predicted student outcomes. This research offers insight into family engagement through two case studies of secondary schools in New York State--chosen for study for their odds-beating graduation outcomes. Educators in these schools share in common the strategies of drawing on local resources and engaging family members in culturally responsive and collaborative ways with particular sensitivities to power imbalances. These findings hold implications with regard to how barriers to family engagement may be overcome in demographically diverse contexts with histories of better graduation outcomes.