The early childhood antecedents and behavior-problem correlates of monitoring and psychological control were examined in this prospective, longitudinal, multi-informant study. Parenting data were collected during home visit interviews with 440 mothers and their 13-year-old children. Behavior problems (anxiety/depression and delinquent behavior) were assessed via mother, teacher, and/or adolescent reports at ages 8 through 10 years and again at ages 13 through 14. Home-interview data collected at age 5 years were used to measure antecedent parenting (harsh/reactive, positive/proactive), family background (e.g., socioeconomic status), and mother-rated child behavior problems. Consistent with expectation, monitoring was anteceded by a proactive parenting style and by advantageous family–ecological characteristics, and psychological control was anteceded by harsh parenting and by mothers' earlier reports of child externalizing problems. Consistent with prior research, monitoring was associated with fewer delinquent behavior problems. Links between psychological control and adjustment were more complex: High levels of psychological control were associated with more delinquent problems for girls and for teens who were low in preadolescent delinquent problems, and with more anxiety/depression for girls and for teens who were high in preadolescent anxiety/depression.