Larissa Pahomov teaches students English and Journalism at Science Leadership Academy in Philadelphia, Pennsylvania. The school opened its doors to students just seven years ago and was designed to encourage both inquiry and critical pedagogy. To those ends, there is a thematic curriculum for each grade level--for sophomores, it's "systems," and the Prisons Unit comes out of this broader, grade-wide thematic curriculum. The essential questions for this year's sophomore curriculum are the following: (1) How are systems created and defined? (2) How do systems shape the world? and (3) What is the role of the individual within the system? This approach means that literature is not just about narrative and vocabulary--it is the medium we use to take a hard look at the world around us and identify the structures that hold it up. Pahomov begins this unit with a quote from Fyodor Dostoyevsky : "The Degree of Civilization in a Society Can be Judged by Entering Its Prisons." The quote greets her tenth grade students when they enter the classroom on the first day of the Prisons Unit. She reads it to them several times, writes it on the board, then leaves them to respond in their journals. When ten minutes have passed, Pahomov asks them for their responses. As a teacher who values critical thinking and getting students to see the bigger picture, she looks forward to pushing their thinking on this topic. This article describes a unit that pairs a canonical text--"Night" by Elie Wiesel--with selections from "Finding Freedom" by Jarvis Jay Masters, an inmate currently on death row, and encourages students to critically examine the purposes and effects of imprisonment.