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It has been noted that one of the distinctive features of prison work is the ability to combine “well-being and discipline”, or “care and power” (Liebling, 2011; Nylander, 2011; Tait, 2011). In fact, the stress derived from having to keep the authority and control, while supporting and taking care of prisoners, has been considered the “permanent dilemma” of prison staff occupational role (Liebling, 2011; Tait, 2011; Nylander et al., 2011). This paper aims to explore prison staff orientations towards prisoners in Uruguay, Latin America, where a prison reform is taking place. This reform consists of, among other changes, moving prisons from police to civilian control, even though policemen are still the majority, not only among prison guards, but also among prison authorities. Using data from the First Prison Staff National Census (2015), which contains multiple items assessing guards’ orientation (Klofas & Toch, 1982; Melvin et al., 1985; Cullen et al., 1989; Liebling, 2011), this paper explores the impact of individual (gender, age, length of service, education) as well as environmental factors (type of prison, role conflict, goal clarity) on staff approaches to correctional work. Results show significant differences between civil and police staff, showing incipient evidence on prison reform outcomes.