Findings show that although distal supervision may decrease on average, it does not decrease the same amount or at the same rate in all families. Moreover, whereas most adolescents were classified into the two groups characterized by low levels or reductions in family rules, only a small portion was classified into the one group characterized by low levels and reduction in monitoring knowledge. In terms of antecedents, membership in the group characterized by low levels and reductions in monitoring knowledge was anteceded by higher levels of behavior problems and living in less safe neighborhoods. In contrast, membership in the group characterized by low levels and reductions in family rule was anteceded by higher socioeconomic status and living in safer neighborhoods. Although low levels and reduction in monitoring knowledge are more common for boys than girls, interactions with sex were minimal, suggesting that antecedents are similar for boys than girls. Results suggest personal and contextual risk antecedes non-normative decreases in monitoring knowledge, whereas contextual risk inhibits normative reductions in family rules. Data were collected from 585 families over a 7-year period covering ages 10 through 16 and living in Nashville or Knoxville, TN, or Bloomington, IN. Tables, figures, and references