The availability and accessibility of programming in penal institutions is an important and revealing element of the nature of these institutions. Critical carceral scholarship points to the dominance of carceral logic in and beyond the carceral setting, but few empirical accounts explore the intricacies of this dynamic. Furthermore, scholarship on the structures of programming is largely nonexistent. This thesis combines original data collection and analysis to establish a state-wide assessment of jail programming in Illinois, finding that programs exist at most but not all jails in Illinois, and that the number and types of programs available vary significantly. It also undertakes an in-depth case study of Cook County Jail, drawing on interviews with program coordinators and facilitators to investigate the factors that affect the availability of and access to programming in a rhetorically progressive jail as well as the relationship of these factors to dynamics of carceral power. This thesis finds that carceral logic shapes the availability and accessibility of programs and even co-opts programs, expanding carceral control through the programming apparatus. These findings indicate that carceral institutions remain foundationally punitive, regardless of their rhetorical framing, and underscore the expansive reach of carceral power.