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This paper explores how teenage parenthood affects students’ high school education attainment, and evaluates the effectiveness of dropout prevention programs that offer on-site childcare. I use data from the High School Longitudinal Study (2009), collected by the National Center for Educational Statistics through the US Department of Education. These data combine survey responses from students, their parents, and school staff. Using school fixed effects and instrumental variable estimation I evaluate the impact of teenage parenthood on the probability of dropout. Female students with a child have, on average, 13.8 percentage points higher likelihood of dropping out of high school. The increased probability is offset by the existence of a dropout prevention that provides childcare. Among female students with children, attending a school with a dropout prevention program that provides childcare is associated with a 28.0 percentage point lower probability of dropping out of high school.