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We analyze the determinants of adolescent motherhood and its effect on high school attendance and completion in a developing country setting. Using eight repeated rounds of Chilean household surveys that span the 1990 – 2006 period, we analyze the role of individual, family and community characteristics in determining teen motherhood. Our regression results reveal that adolescents who were born to teen mothers, who live in poorer households and in single-mother families, are more likely to have children. The availability of full-time high schools reduces the likelihood of teen motherhood among low-income girls. In the second part of our empirical exercise, we estimate the effect of being a teenage mother on the probability that girls attend or complete high school. To control for possible endogeneity between teen pregnancy and schooling outcomes, we use an instrumental variables approach. Our results reveal that after controlling for individual, family, and community characteristics, being a mother reduces the probability of high school attendance and completion by 0.17 to 0.26 (21 to 31 percent), making it the most important determinant of high school desertion. This implies that policies aimed at reducing early childbearing will have immediate, strong effects on girls’ school attainments.