The present study examined parental support and monitoring as they relate to adolescent outcomes. It was hypothesized that support and monitoring would be associated with higher self-esteem and less risky behavior during adolescence. The diverse sample included 16,749 adolescents assessed as part of the National Educational Longitudinal Study. Both high parental support and parental monitoring were related to greater self-esteem and lower risk behaviors. The findings partially confirm, as well as extend, propositions in attachment theory.