Studies using valid measures of monitoring activities have not found the anticipated main effects linking greater monitoring activity with fewer behavioral problems. This study focused on two contexts in which monitoring activities may be particularly influential. Early adolescents (n = 218, M age = 11.5 years, 51% female, 49% European American, 47% African American) reported their unsupervised time, beliefs about the legitimacy of their parents’ authority, and their own involvement in antisocial behavior. Mothers and adolescents reported their perceptions of adolescent disclosure and parental solicitation and control. Adolescents’ perceptions of greater parental solicitation at age 11 were associated with less antisocial behavior at age 12 (when controlling for age 11 antisocial behavior) among adolescents reporting large amounts of unsupervised time and weak legitimacy beliefs. Perceived parental solicitation may be an effective deterrent of antisocial behavior when adolescents spend a lot of time unsupervised and for adolescents who are likely to challenge the legitimacy of their parents’ authority.