The notion that policing and incarceration are permanent and necessary, if in need of reform or more “humane” design, guides contemporary practices of making in a range of design fields and, increasingly, designers’ forays into policy- and government service-making. These projects often take the form of spatial interventions and proposals for new jails, police stations, and, in some cases, the reorganization of the spaces around them. This article examines three projects—Chicago’s Polis Station, the New York City Justice Hubs, and the Oakland Power Projects—that contend with the infrastructure of the prison industrial complex, in part by asking people questions about policing and incarceration to envision what to build. Here, I focus on what shaped these questions, and how the questions in turn shaped the possibilities for design that emerged from them, in ways that matter deeply to the imbrication of architecture, design, and punishment.