Parents have adopted a variety of strategies for monitoring their adolescent children; yet, some strategies are more strongly associated with risk-taking during adolescence. The present study examined how age moderates the association between parental monitoring and adolescent risk-taking. Participants (N = 117, Mage = 15.21 years) were predominantly female (64.1%), and the largest racial/ethnic group in the sample was Asian (57.3%). Participants’ reports of risk behavior were regressed on participants’ reports of parental monitoring, and age was explored quadratically as a curvilinear moderator. Among more frequently monitored adolescents, risk-taking was lower in mid-adolescence and higher in later adolescence; among less frequently monitored adolescents, risk-taking was higher in early and mid-adolescence and lower in later adolescence (R2 = 0.26, p < 0.01). Parents should consider age-related developmental changes in adolescence (e.g., increased need for autonomy) and modify their monitoring efforts to match youths’ developmental needs.