This study documents patterns of contact between juvenile probation officers and parents and examines factors associated with officer judgments about parental cooperation. Data for the study was derived from a Web-based survey of probation officers (N = 308) who reported their use of probation strategies with specific youths identified from their caseloads. Results showed that parent contacts were predicted by parent and youth drug use, parent and youth cooperation, and officer attitudes favoring punishment. Parental cooperation with probation processes was predicted by youth and parent drug use problems, parent offending history, youth cooperation, and race. Results of this study point to the need for evidence-based strategies to promote parental involvement for high risk and high need families. (Contains 3 tables and 1 figure.)