This article reports on the challenges teachers face when working with juveniles who are incarcerated. For example, they must devise an English curriculum that can help students develop reading and writing skills while also becoming literate about the prison industrial complex and the ways that it governs their lives. Teachers struggle to find ways of making these topics new and powerful while also challenging students to see how learning about the system is an important form of literacy. They also face structural constraints that make it difficult to create cohesive, intellectually rich units of instruction. Students at the juvenile justice center come and go, sometimes very quickly and sometimes not nearly quickly enough. Learning is constantly interrupted, and making sure that all students can learn in this constantly changing setting is challenging. Another challenge is that the students often view school as part of the institution that they must try to resist. Many students in the Juvenile Justice Center have experienced very little success in school, and they may even fault the school system for failing to help them keep their dreams from being deferred. The authors also report on the good that has come from teachers reflecting on their unique roles such as: (1) viewing their work as a unique opportunity to help students connect critical social inquiry to their own lives through self-examination and reflection in order to question their place in the criminal justice system; (2) learning that smaller, self-contained projects are more successful because they give the students a sense of completion and accomplishment; (3) helping students improve academically, because the curriculum is relevant and that their experiences, opinions, and backgrounds are being respected; and (4) working with students on the fringe taught them that children crave opportunities to learn and share their stories even in unlikely places like jails.