The chaplain, with a religious background practicing pastoral care, plays a role that conflicts with the norms of the secular institution that formally employs him. In this regard, prison is a highly challenging workplace. Drawing on qualitative data, we examine the position and identity of the prison chaplain in the Czech prison system. We argue that the main source of tension within the workplace is the chaplain’s profound interest in a prisoner’s personal life. This tendency is in a clear contrast with the intentions of the punitive prison system. Examples the potential of chaplain’s role are also discussed.