As political tides shift and funding for college-in-prison programming ebbs and flows, educators who work in these contexts are often left with few resources for questioning their practice and their field. To that end, this book aims to encourage dialogue, to ask educators to interrogate their values, beliefs, and practices with and about college-in-prison programming and the students those programs serve. By consulting the works of Paulo Freire and Ernst Bloch, this text seeks to present a methodology for best designing and implementing a meaningful literacy pedagogy for incarcerated students at the nexus of social, political, and educational contexts.