Using multivariate techniques, the authors investigate how age, family type, and race/ethnicity affect grandmother-headed families’ economic resources. The authors examine four grandmother-headed family types that are classified on the basis of two features: parents’ presence and the caregiving relationship of the grandmother and grandchild. Using data from the 2000 census (Public Use Microdata Sample 5%) to predict grandmother-headed families’ official and relative poverty statuses, analyses indicate that age, race/ethnicity, and family configuration are major explanations for poverty differences. The effects of race/ethnicity on official and relative poverty are greater among older cohorts than among the youngest cohorts. Additionally, the effects of age on poverty vary by family type: the lower chances of poverty that are associated with older cohorts are not as great among two-generation families as they are among three-generation grandmother-headed families. The authors interpret these findings using a life-course perspective and cumulative disadvantage theory and discuss the implications for grandmother-headed families’ economic security.