Objectives. Middle-aged parents’ well-being may be tied to successes and failures of grown children. Moreover, most parents have more than one child, but studies have not considered how different children's successes and failures may be associated with parental well-being.Methods. Middle-aged adults (aged 40–60; N = 633) reported on each of their grown children (n = 1,384) and rated their own well-being. Participants indicated problems each child had experienced in the past two years, rated their children's successes, as well as positive and negative relationship qualities.Results. Analyses compared an exposure model (i.e., having one grown child with a problem or deemed successful) and a cumulative model (i.e., total problems or successes in the family). Consistent with the exposure and cumulative models, having one child with problems predicted poorer parental well-being and the more problems in the family, the worse parental well-being. Having one successful child did not predict well-being, but multiple grown children with higher total success in the family predicted enhanced parental well-being. Relationship qualities partially explained associations between children's successes and parental well-being.Discussion. Discussion focuses on benefits and detriments parents derive from how grown progeny turn out and particularly the implications of grown children's problems.