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Prison workers’ role in “modern” prison systems can be described as a form of peacekeeping, based on institutional legitimacy, communication, and building of relations with prisoners. Their main product is not security or control but personal interaction between them and prisoners. A comparative study focusing on the dynamic nature of legitimacy in prisons and relations between prison actors was implemented in the only prison for women in Slovenia in 2015 and 2023, where 29 prisoners were interviewed. In general, the results of the qualitative comparative analysis showed that prisoners perceive prison workers as legitimate power holders and develop good relations with them. Obtaining benefits and avoiding sanctions were identified as primary reasons for prisoners’ cooperating with prison workers and compliance with their decisions. The findings exposed differences in prisoners' perception of prison workers’ fairness, as well as, the nature of prison staff-prisoners’ relations in studied periods.