Objectives. This study investigated predictors of discrepancies in reports of 5 types of support that aging parents and their middle-aged children exchanged with one another. Predictors included structural factors, including needs and resources and dyadic characteristics, and psychological factors, including family obligation and investment in the relationship.Methods. Participants included 337 dyads of parents (aged 59–96 years) and their children (aged 40–60 years). Multilevel models assessed the level of discrepancies between dyadic members and examined predictors accounting for the discrepancies. We considered downward (from parent to child) and upward (from child to parent) directions in support exchanges.Results. For upward support from adult children to their parents, children reported that they gave more than their aging parents reported receiving. For downward support from parents to children, the results differed depending on the type of support. Discrepancies between parents’ and children’s reports were associated with parents’ feelings of obligation toward children and children’s ratings of the importance of parent–child relationship.Discussion. These results suggest the importance of considering multiple perspectives and the direction of exchanges between generations. Discrepancies in reports of support reflect both self-enhancement and family context and may be an important source of misunderstanding and conflict between generations.