This article published in Global Public Health by Lindsay Stark and colleagues examines the impact of care structures on adolescent sexual behaviors. Orphanhood is common in sub-Saharan Africa, therefore it is critical to understand the fluidity of care. In fact, many 'orphaned' children have a surviving biological parent. This study examines the protective effects of family-level factors on early sex and pregnancy in rural Sierra Leone. A survey of 530 adolescents in 2 districts in Sierra Leone was analyzed to evaluate associations between living arrangement and orphanhood on recent sexual activity and pregnancies out of wedlock. After controlling for confounders, living with one's mother and living with both parents were protective against recent sexual activity. Orphan status was not significantly associated with recent sexual activity. Among 164 sexually active adolescents, neither living arrangement nor orphanhood was associated with pregnancy. This study demonstrates the protective effect of living with a surviving biological parent to delay early sexual debut. Once an adolescent becomes sexually active; however, living arrangement is not associated with the risk of pregnancy out of wedlock. The findings suggest that supporting family connectedness and preventing unnecessary family separation may benefit at least some aspects of adolescent sexual and reproductive health in Sierra Leone.