Compared to their housed counterparts, homeless youth become pregnant at exceptionally high rates. Causes of such pregnancies are multifaceted, while a paradoxically high proportion of these pregnancies are intended. This review discusses causes and risk factors associated with homeless youth pregnancies, and notes experiences of pregnancy decision-making discord, challenges encountered during and following pregnancy, and difficulties faced by homeless youth when or if they become parents. Because homeless youth face a wide array of unique risks, future research would benefit from exploring alternative approaches to prevention to reduce pregnancies and improve sexual and reproductive health outcomes among this population.