Synthesizing concepts and theories from critical organization studies with those that have informed criminological studies of prison design and the lived experience of imprisonment, the article discusses the ways in which the architecture and aesthetics of penal environments might be better understood with reference to the restricted economies of space found in industrial and bureaucratic organizations. It is argued that a grasp of the limits historically placed on the subjective growth of individual workers (workspaces frequently being characterized as 'iron cages' or 'psychic prisons') can enhance our understanding of the physical and psychological confinement of those in custody. Moreover, critical organization studies can inform emerging debates about what future prisons should look like and alert us to the potential fallacy in assuming that 'modern' equates to 'better'. While clean, humane and safe environments are unquestionably desirable for both prisoners and prison staff, and considerations such as natural daylight, access to outside space and aesthetic stimuli are increasingly being incorporated into penal environments around the world, this article will critically interrogate the value of such initiatives arguing that they may, in fact, represent a new and potentially more insidious form of control that bring their own distinctive 'pains'. (Published Abstract)