The present study examined whether internalizing and externalizing symptoms may mediate the association between adolescent-mother and adolescent-father attachment and substance use. The sample included 167 adolescents (47% girls) who were assessed at five time points with approximately 1 year between each assessment, beginning in middle adolescence (Mage=14.07) and ending in the transition to young adulthood (Mage=18.39). The adolescents reported their perceived attachment with both their mother and father during middle adolescence (Times 1 and 2), their internalizing and externalizing symptoms during late adolescence (Times 3 and 4), and their alcohol use during the transition to young adulthood (Time 5). The results showed that less secure adolescent-father attachment, but not adolescent-mother attachment, was predictive of heightened externalizing and internalizing symptoms. In turn, heightened externalizing symptoms were predictive of heightened alcohol use. Despite the nonsignificant direct association between adolescent-father attachment and alcohol use, less secure adolescent-father attachment was indirectly predictive of greater alcohol use, mediated through heightened externalizing symptoms. The findings highlight the importance of close and trusting father-adolescent relationships in the development of psychopathology and substance use behaviors. The developmental cascade from a less secure adolescent-father attachment to greater externalizing symptoms and heightened substance use, as well as implications for prevention and intervention of young adult substance use, are discussed. RESEARCH HIGHLIGHTS: The differential pathways from adolescent-mother and adolescent-father attachment to substance use during the transition to young adulthood are not well known. Longitudinal data were used to test whether internalizing and externalizing symptoms may mediate the association between adolescent-mother and adolescent-father attachment and substance use. Less secure adolescent-father attachment predicted heightened internalizing and externalizing symptoms, and less secure adolescent-father attachment predicted greater alcohol use, mediated through heightened externalizing symptoms. The findings suggest that addressing insecure attachment with fathers during adolescence may reduce unhealthy substance use during the transition to young adulthood.