Current research and theory suggest that the healthy path of autonomy development involves gradual negotiation of adolescents' independence "within" a context of continued family connection. This theory-generating study examined the role that adolescents' participation in youth programs plays in these adolescent-parent negotiations. Qualitative data from high-school-aged youth in 12 programs and from a sub-sample of parents were analyzed employing methods of grounded theory. These analyses suggest that program participation provides a pathway of opportunities for youth to exercise individual choice and develop qualities of self-reliance with parental approval. In turn, parents' observation of self-reliance in the program and youth's demonstration of these qualities in family interactions can lead to changes in adolescent-parent relationships that provide youth greater family autonomy with connection.