This volume makes a case for engaging critical approaches for teaching adults in prison higher education (or “college-in-prison”) programs. This book not only contextualizes pedagogy within the specialized and growing niche of prison instruction, but also addresses prison abolition, reentry, and educational equity. Chapters are written by prison instructors, currently incarcerated students, and formerly incarcerated students, providing a variety of perspectives on the many roadblocks and ambitions of teaching and learning in carceral settings. All unapologetic advocates of increasing access to higher education for people in prison, contributors discuss the high stakes of teaching incarcerated individuals and address the dynamics, conditions, and challenges of doing such work. The type of instruction that contributors advocate is transferable beyond prisons to traditional campus settings. Hence, the lessons of this volume will not only support readers in becoming more thoughtful prison educators and program administrators, but also in becoming better teachers who can employ critical, democratic pedagogy in a range of contexts.