Children's representations of family relationships were examined in relation to grandparent responsivity and depression, family sociodemographic risks, and children's behavior problems in custodial grandparent families. Using multiple methods, data were collected from 79 families with children aged 3 to 7.5 years. In 37 families, children were raised by grandparents as the result of maternal incarceration and, in 42 families, children lived with grandparents because of other parental problems. Results indicated that children with representations of less optimal family relationships and children whose grandparents were less responsive to them at home were more likely to exhibit externalizing behavior problems. In addition, children were more likely to include relationship violence in their story stem enactments when grandparents reported elevated depressive symptoms. Results suggest links among grandparent depression, quality of children's family relationships, and children's behavior problems in grandparent-headed households.