This study examined the moderating effect of risk on the relation between autonomy processes and family and adolescent functioning. The present sample comprised 131 adolescents from either a low-risk or high-risk social context, their mothers, and their peers. Observational ratings of autonomy processes within the mother-adolescent dyad were obtained, along with adolescent reports of the quality of the mother-adolescent relationship, and both adolescent and peer reports of the adolescent's functioning. Consistent with past research, in low-risk families, behavior undermining autonomy was negatively related to relationship quality, and adolescents' expressions of autonomy were linked with positive indices of social functioning. In high-risk families, however, undermining of autonomy was positively linked with mother-adolescent relationship quality, and adolescents' expressions of autonomy were linked with negative indices of social functioning. Results are interpreted as demonstrating the ways in which the developmental task of attaining autonomy in adolescence is systematically altered depending on the level of risk and challenge in the adolescent's social context.