Research on pregnancy and sexual health among homeless youth is limited. In this study, qualitative interviews were conducted with 41 homeless young injection drug users (IDUs) in Los Angeles with a history of pregnancy. The relationship between recent pregnancy outcomes, contraception practices, housing status, substance use, utilization of prenatal care, and histories of sexual victimization are described. A total of 81 lifetime pregnancies and 26 children were reported. Infrequent and ineffective use of contraception was common. While pregnancy motivated some homeless youth to establish housing, miscarriages and terminations were more frequent among youth who reported being housed. Widespread access to prenatal and medical services was reported during pregnancy, but utilization varied. Many women continued to use substances throughout pregnancy. Several youth reported childhood sexual abuse and sexual victimization while homeless. Pregnancy presents a unique opportunity to encourage positive health behaviors in a high-risk population seldom seen in a clinical setting.