The over-time reciprocal links between parenting and adolescent adjustment were examined in a sample of 1,354 serious adolescent offenders followed for 3 years (16 years of age at baseline, SD = 1.14). Parallel processing growth curve models provided independent estimates of the impact of parenting on adolescent functioning as well as the impact of adolescent functioning on parenting. Positive adolescent development was facilitated by high parental warmth and low parental hostility. Parental monitoring predicted less problematic behavior, but less positive functioning as well. Predictably, parents became warmer and less hostile in response to positive adolescent development, and less warm in response to problematic adolescent functioning. Parental monitoring declined when adolescents exhibited either positive or problematic functioning.