In this article, Michael Brawn, an incarcerated student, and Erin L. Castro, a nonincarcerated instructor, engage in a dialogue about the politics of using critical pedagogies in prisons, where teaching and learning processes are severely restricted by the constraints of mass incarceration. Situated within the broader politics of postsecondary educational opportunity for incarcerated people, their dialogue highlights the ways that the prison context significantly limits the promises and praxis of critical pedagogies. The authors close by turning to an emplaced praxis for nonincarcerated educators working within prison systems that acknowledges the complicated and contradictory nature of authority in critical pedagogies.