The article explores the role of discretion in the distribution of privileges in prison, the results of an exploratory observational research project in a maximum-security prison, and the implications of the findings for penology. The policing literature, with its emphasis on “law in action,” peacekeeping, the need for community consent and the observed social practices of “low visibility” police officers, offers some useful sensitizing tools to apply to the less researched practices of prison officers. Many relevant issues arise: the use of informal rules, the significance of “talk,” and the need for scrutiny and management of discretion. Important aspects of prison life include the role of relationships, which are arguably “instruments of power,” and the shifting power base of prison staff away from exchange and accommodation towards coercion. There is a gulf between the rule-following or compliance model of prison work favored by risk-averse officials and the negotiation model actually delivered by most prison staff. The sociology of prison life needs to turn its attention to these significant and changing forms of the penal enterprise. Notes, references