Evaluations of extended day programs in underserved communities have shown that participants usually drop out by the time they are 11–12 years old. Most of these programs, especially those that focus on physical activity, do not promote broadly developmental and empowerment-based processes and outcomes advocated by the emerging field of youth development. This article investigates both the retention issue and youth development processes and outcomes for two sequential physical activity extended day programs in an underserved community. Retention data and participant program evaluations were collected over a nine-year period, and these data together with a selective review of related studies are analyzed to determine the extent of linkage between the promotion of positive youth development and retention beyond 11–12 years old.