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The capacity of penal officers to exercise authority with legitimacy is fundamental to the administrative and moral performance of prisons and jails. Scholars argue it is through interactions between officers and detainees that authority is practiced, policy is enacted, and penal culture is produced. This study examines the nature of daily encounters between jail officers and detainees in a large, urban jail system. Based on the results of an anonymous survey of jail officers, a cluster analysis of hostile, friendly, and cooperative encounters identified three patterns of interactions. Consistent with Leibling’s (1991) theoretical framework, jail officers exhibited three supervision styles: enforcers, professionals, and reciprocators. Further, we show that supervision style is associated with attitudes about the use of force, support for procedural justice, correctional ideology, and job satisfaction.