Pregnancy rates among women in the U.S. who are homeless are much higher than rates among women who are housed (Greene & Ringwalt, 1998). Yet little research has addressed mental health, risk and resilience among young mothers who are homeless. This study utilizes a sample of women from the Midwest Longitudinal Study of Homeless Adolescents (MLSHA) to investigate pregnancy and motherhood over three years among unaccompanied homeless young mothers. Our data are supplemented by in-depth interviews with a subset of these women. Results show that almost half of sexually active young women (n = 222, µ age = 17.2) had been pregnant at baseline (46.4%), and among the longitudinal subsample of 171 women (µ age = 17.2), almost 70.0% had been pregnant by the end of the study. Among young mothers who are homeless, only half reported that they helped to care for their children consistently over time, and one-fifth of the women reported never seeing their children. Of the young women with children in their care at the last interview of the study (Wave 13), almost one-third met criteria for lifetime major depressive episode (MDE), lifetime posttraumatic stress disorder (PTSD), and lifetime drug abuse, and one-half met criteria for lifetime antisocial personality disorder (APD). Twelve-month diagnoses are also reported. The impacts of homelessness on maternal and child outcomes are discussed, including the implications for practice, policy, and research.