By the ninth century, the prison had become more than a place of detention and rehabilitation: it was a theater of punishment. Danger surrounded the prison, an institution meant to be both symbolically visible to the public yet structurally defensible; where people went to vent social and political frustrations and where policing authorities tried to contain and isolate criminal elements. Though previous scholarship has addressed the institutional origins of the prison and the development of criminal law in the ninth century, the prison as a site of urban resistance has been largely overlooked. Cracks in the Abbasid regime began to emerge as political control became decentralized and vested between competing administrators jockeying over money, power, prestige, and vainglory. Tulunid governors began to exercise regional and judicial autonomy in Egyptian Fustat in the second half of the ninth century, reinterpreting political ceremonies and building urban areas of discipline and justice all in an effort to affirm territorial sovereignty. This period witnessed massive changes in the administration and in the urban geographies of the Abbasid capital (Baghdad) and Fustat, changes that impacted the carceral regime. These bureaucratic shifts in power and hierarchy could be felt on the ground, at prisons which became more diverse and responsive to the rise of crime and the anxieties of the public. This paper explores the social and administrative changes occurring as the prison became an embodiment of punishment. Capturing the dynamic social and administrative shifts in the medieval Islamic prison requires a robust range of sources such as political and biographical literature, administrative and jurisprudential treatises, and urban geographies. Looking at different Islamic contexts such as Baghdad and Fustat, the paper prioritizes a comparative angle to show the broader impact of penal prosecution, punishment and reform in the medieval Middle East. The prison exposes a punitive relationship between governing authorities and civilians, where policing officials disciplined criminals and displayed corpses in a way that educated the public and where locals staged protests and assaulted prison walls and gates to engage in resistance and social reform.