The secure base construct represents one of attachment theory’s most important contributions to our understanding of parent–child relationships and child development. The present study represents the first examination of how parents’ self-reported attachment styles relate to parental secure base provision and adolescent (mean age = 16.6 years, SE = .59) secure base use during an observed parent–adolescent interaction. Further, the present study is the first to examine how fathers’, as well as mothers’, attachment styles relate to observed behavior in a parent–child interaction. At the bivariate level, maternal avoidance, but not anxiety, was negatively associated with observed adolescent secure base use. In addition, path analysis revealed that maternal avoidance was indirectly related to less adolescent secure base use through mothers’ self-reported hostile behavior toward their adolescents and through adolescents’ less positive perceptions of their mothers. Further, paternal anxiety, but not avoidance, was indirectly related to less adolescent secure base use through fathers’ self-reported hostile behavior toward their adolescents. No significant findings emerged in relation to parental secure base provision. We discuss these results in the context of attachment theory and suggest directions for future research.