We analyze the effect of mothers’ and youths’ reports of family financial stress and conflict on youths’ transitions into adult roles. We find that mothers’ reports of financial stresses and borrowing constraints are associated with earlier transitions to inactivity and public assistance, while youth reports of financial stresses are associated with earlier nest-leaving. Youths reporting conflict with parents leave school and move out earlier than their peers, while conflict between parents is associated with youth making later transitions. Overall, financial stress and conflict have independent effects on youths’ transitions and youths’ perspectives have different consequences to those of their mothers.