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This study explored the family and community engagement activities in support of student well-being and academic achievement. Using the positive psychology framework PERMA(H), eleven semi-structured interviews were analyzed. The findings illuminated that focused attention on student attendance and well-being preceded high achievement gains. Nine specific insights were useful in cultivating a positive parent and community engagement plan. Significantly, strategic plan elements and recommendations that may be beneficial to other urban districts seeking to engage families in support of student well-being and achievement gains, were identified. Mobilizing interdisciplinary bodies of evidence and strategies addressing student needs through powerful narratives informs professional practice while adding to school leadership, parent and community engagement, and positive psychology literature.