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Considering the polarized socio-political climate in the U.S., engaging Black students and their families may prove to be challenging for some school-based leaders. It is imperative that school leaders seek to understand the students they serve and factors outside school that may impact academic and social-emotional well-being. In this qualitative study, P-12 leaders were interviewed to gain a deeper understanding of the challenges, barriers, and successes of engaging Black families to improve student outcomes. Findings indicate the need for educators to be involved in continuous cultural competence training, 2) increase communication and partnership with families, 3) improve relationships with students, and 4) monitor school climate. These findings have implications for improving research, policy, and practice of family engagement in education.