Abstract The Czechoslovak prison system is closely bound up with the political situation, and period before the year 1989 was no exception. Its transformation reflects changes in society and politics. The role of the prison system, attitudes to prisoners, as well as modernising trends are all a reflection of the dominant master narratives of that time. This study examines how university-educated employees who were in expert positions within the prison system (psychologists, doctors, a librarian, educators, top management) between 1965 and 1992 adapted to the prison system in place or tried to transform it at the time, and how they reflect on their engagement with it at present. By exploring these questions, we are ultimately asking how their experience as prison staff in communist prisons influenced their professional (narrative) identity and course of life, and how dominant social and political narratives under the communist rule impacted their individual lives. The study adopts a qualitative, idiographic and social constructivist narrative engagement approach to capture the interplay between the prison system and individuals within it. It finds that former employees constructed three different identity configurations reflecting their engagement with the prison system. The consequences of these configurations for prison employees, prison system and society in general are discussed.