In this book we report the experience of prison guards in a maximum security prison complex. We analyze elements that characterize a framework of evidence of phronesis, described in Aristotelian philosophy as the virtue of practical order that presupposes deliberation in critical situations, where agents’ rationality is limited by very specific contexts of action. The notion of phronesis illuminates new perspectives for understanding rationality in contingent circumstances of organizational praxis. This is an investigation undertaken from a microsociological analysis of agents’ practices in prison work, based on interviews, field observation, and document analysis. The results of this study illustrate evidence of phronesis from the analysis of the agents’ experience in containing the actions of organized crime inside the prison complex and the effects produced in the management based on this experience.