The introduction opens with an Inside-Out Prison Exchange class in 2019, a college course that brings undergraduate students inside prisons to study with incarcerated students. Reflecting on the rarity of such an encounter, the introduction argues that prisons walls have not always been impermeable, and that permeability has been both a vehicle for social control and a way for prisoners to resist such control. Following a description of a 1968 tour by “traveling ambassadors” from the Louisiana State Penitentiary at Angola, the introduction explains how clemency, conjugal visits, and furloughs help us understand changing ideas of risk and rehabilitation; allegiances across political categories; geography of prison practices across time and place; connections between penal practices and welfare policies; and prisoners’ sense of their own entitlements, relationships, and transformation.