Using motivational theories of engagement and adopting a multidimensional perspective of academic engagement, the authors investigate the associations among teacher and parent support, students’ academic self‐efficacy, and academic engagement among a sample of reconnected youth who have returned to academic pursuit after dropping out (N = 938, mean age = 16.50, SD = 1.78). In addition, they examine how youth's adverse life experiences moderate the pathways in this model, an analysis notably missing from much of the academic engagement literature. They find that students’ academic self‐efficacy mediates parent and teacher support and youth academic engagement. Moreover, participants’ adverse life experiences moderate the connections among perceived support from parents, academic self‐efficacy, and academic engagement. Implications for practice and future directions are discussed.