Adopting an asset-based and resilience-building framework, the present study examines the effects of out-of-school activities on advancing the academic achievement, leadership skills, and service orientation of youth of color placed at risk who attended one of over 60 independent urban middle schools that follow the NativityMiguel model of education. These out-of-school activities include late afternoon and evening academic support and other activities, such as sports and clubs, community service activities, and a holistic summer enrichment program. The present study summarizes results of individual and small group interviews with graduates and staff that address the benefits of the out-of-school programs. These benefits include being prepared for later academic success, developing effective leadership skills, belonging to a community of supportive faculty and peers, and developing a strong commitment to service and activism oriented toward addressing the needs of underserved communities. Also addressed are staffing and planning issues that contribute to successful out-of-school programs and implications for including these efforts in other schools.