Groups of adolescents were identified on the basis of developmental trajectories of their families' rules and their parents' knowledge of their activities. Characteristics of the adolescent, peer antisociality, and family context were tested as antecedents. In sum, 404 parent-adolescent dyads provided data for adolescents aged 10-16. Most adolescents were classified into groups characterized by low levels and reductions in family rules over time. However, low socioeconomic status and residence in unsafe neighborhoods increased membership in the group characterized by consistently high levels of family rules. Most adolescents were assigned membership in groups characterized by relatively stable moderate-to-high levels of parental knowledge of their activities. However, greater externalizing problems and peer antisociality, as well as residence in an unsafe neighborhood, increased membership in the group characterized by low and decreasing levels of knowledge. Results suggest that personal and contextual risk antecedes nonnormative decreases in parental knowledge, whereas contextual risk inhibits normative reductions in family rules. (Contains 4 tables and 2 figures.)