The purpose of this study was to test whether parenting style as conceptualized through Self-Determination Theory (SDT) moderates the association between parental monitoring and adolescent problem behavior. Self-reported data from adolescents (n = 242; 49.2% male; M age = 15.4 years) and their parents (n = 276; 70% mothers) were used in the study. Results showed that monitoring through questions, but not through rules, was significantly associated with behavior problems. Adolescent-reported monitoring through questions, but not parent-reported, was linked to less problem behavior. Also, parental autonomy support and involvement were linked to less problem behavior. Results showed that two out of 24 interactions between monitoring and style variables were significant. Specifically, the links between higher adolescent-reported monitoring through questions and parent-reported autonomy support, and between parent-reported monitoring through rules and adolescent-reported structure were significant. However, neither pattern was consistent with expectations.