The first goal of the present study was to examine how mothers' and fathers' self-reported attachment styles relate to how they perceive themselves as parents and to their ability to serve as secure base for their adolescent children. The second goal was to examine how parents' attachment styles relate to adolescents' perceptions of their parents and to observed adolescent secure base use with each parent. Path analyses revealed that greater parental insecurity predicted parents' negative perceptions of themselves as parents. Further, maternal avoidance and paternal anxiety were significantly indirectly related to observed secure base provision through parents' perceptions of hostility toward their adolescent. In addition, parental attachment styles significantly predicted adolescents' perceptions of mothers, but not fathers. Further, maternal avoidance was significantly indirectly related to adolescent secure base use through adolescent perceptions of their mothers. These results advance the growing body of literature demonstrating an important link between parents' self-reported attachment styles and various facets of parenting.