Why does a public high school, despite having resources and educators with good intentions, end up graduating English learners (ELs) without preparing them for college and career? This book answers this question through a longitudinal ethnographic case study of a diverse high school in Pennsylvania. The author takes the reader on a journey with seven EL students through their last two years of high school, exploring how and why none of them reached the postsecondary destinations they originally aspired to. This book provides a sobering look into the systemic undereducation of high school ELs and the role of high schools in limiting their postsecondary options.