This article uses the concept of a progressive jail assemblage to think about the focus on jails as both a target of social justice organizing and a tool for advancing social justice goals. Drawing on ethnographic research conducted among formerly incarcerated organizers and their allies in Western Massachusetts (New England), I explore how the sheriffs who operate jails in this region, along with their collaborators, have increasingly sought to redefine the figure of the criminal as not just a danger to others but also a danger to themselves, someone in need of rehabilitative treatment and even care. In doing so, these sheriffs have attempted to reinvent their role, from the quintessentially American crime fighting figure, to one who is also a provider of care. Social justice activism has helped to expand the “caring” role of the jail, through increased addiction treatment, re-entry support, and community outreach – even to the extent of incarcerating individuals dealing with addiction who have not been charged with a crime. As progressive jails have been reconfigured as providers of care, abolitionists are confronted with the ongoing dilemma of how to remain a figure opposed to the use of prisons and jails without being seen as against care.