There has been an increase in grandparents raising their grandchildren due to parental absence. This family structure has affected urban, single, low income African Americans at a higher rate than any other racial group. Research on grandchildren reared in grandparent-headed families (GHF) states these children are at risk for significant emotional, behavioral, physical problems, and learning disabilities than children living with their biological parents. The purpose of this study was to explore the experiences of African American grandchildren raised in GHF. Both quantitative and qualitative methodology was used, including individual interviews with 14 African American grandchildren ages 10-16 and their 6 grandparent caregivers, and the completion of the Child Behavior Checklist (CBCL), which is a standard psychological measure. Results indicated that although the majority of the grandchildren were content living with their grandparents, they experienced challenges at school, including behavioral issues, low academic performance, and suspensions. Family factors that might affect grandchildren’s adjustment to living in a GHF are discussed, as well as implications for therapists and recommendations for future research with grandchildren from GHF.