The author teaches in an alternative school in Boston Public Schools and works with students who had dropped out, transferred, or been expelled from their previous schools. Many of her students struggled with reading complex texts and had never learned how to make and defend an argument through their writing. She was determined that they would leave her class confident about their research, reading, and writing skills, and the proud possessors of a portfolio that demonstrated those skills. In this article, the author describes how she engaged the students. Studying the prison industrial complex was valuable for students on a personal, political, and academic level. The class offered students the opportunity to move beyond pathologizing their own lives, families, and communities by helping them put their experiences in a broader social context--an experience that was deeply strengthening for both the students and the author. (Contains 7 resources and 2 online resources.)