Using the 2001 Survey of Income and Program Participation, the current study examines poverty and material hardship among children living in 3-generation (n = 486), skipped-generation (n = 238), single-parent (n = 2,076), and 2-parent (n = 6,061) households. Multinomial and logistic regression models indicated that children living in grandparent-headed households experience elevated risk of health insecurity (as measured by receipt of public insurance and uninsurance)--a disproportionate risk given rates of poverty within those households. Children living with single parents did not share this substantial risk. Risk of food and housing insecurity did not differ significantly from 2-parent households once characteristics of the household and caregivers were taken into account.