Prior research suggests that parents’ monitoring behaviors are related to the conduct problems of children but not to the conduct problems of children with callous-unemotional traits. However, these studies have been cross-sectional. The present short-term longitudinal study investigates the bidirectional influences of parental monitoring and youth problem behaviors, while also examining the potential moderating influence of callous-unemotional traits. We assessed adolescents (Mean age = 14.5 years; SD = 1.8) and parents at two time points. Youths reported their callous-unemotional traits and delinquency, while parents reported their child’s conduct problems, and their parenting behaviors to track and control their child’s activities. We found support for a child-driven change in parents’ monitoring behaviors over time. Specifically, children with high callous-unemotional traits had parents who reduced their monitoring behaviors over time, and their different types of monitoring behaviors were less synchronous over time. In addition, parents of youths with high callous-unemotional traits showed a trend toward not being stable in their surveillance efforts over time. Moreover, greater behavioral control for youths high on callous-unemotional traits did not lead to parents’ greater knowledge about their youths. In fact, having less knowledge was related to decreases in parental control, when youths were high on callous-unemotional traits. The present study supports the importance of personality in shaping how parents actively monitor their children.