Research has supported the prominent influence of attachment security on many facets of adjustment; however, findings are primarily based in examining attachment with mother in infancy. Moreover, examining the context in which attachment and adjustment develops, the role of the father in child development, and the importance of identifying domains of adjustment that are salient to attachment have been neglected. This study investigated longitudinal associations between attachment, observed in a Strange Situation procedure, with mother and father simultaneously and domains of socio-emotional adjustment and psychopathology during the early school years. Analyses indicated insecurity with mother was associated with externalizing behavior and school adjustment difficulties, while insecurity with father was associated with friendship difficulties; the interaction was not associated with adjustment. Findings have important implications for examining family and developmental contexts to understand the influence of attachment on adjustment.