Introducing new approaches based on humane and respectful treatment of prisoners has significantly changed prison workers’ roles and self-image. In this complex environment, prison workers seek recognition of the legitimacy of their authority due to the understanding that order based on prisoners’ normative compliance is stronger and more resilient than prisoners acknowledging prison rules and following staff orders due to fear of losing benefits and sanctions. Findings confirmed previous indications that antecedents of police officers’ self-legitimacy cannot be [simply] applied in a modified form to the prison context. In contrast to other cultural and social environments, the influence of self-legitimacy on prison workers’ support for rehabilitation and harsh treatment of prisoners, including willingness to use force was marginal. By testing different models for measuring self-legitimacy and its antecedents, the influence of the cultural setting on prison workers’ perception of their own legitimacy was confirmed, and testing self-legitimacy in two time periods provided much-needed empirical support for theoretical argument on the effects of social contexts on legitimacy. The study provided empirical evidence that confirmed the unstable nature of self-legitimacy present [even] in a coercive and highly conservative prison environment.