The exercise of parenthood in inmates is an unattended problem in the Chilean prison population. Studies on this subject are limited and do not delve deeply into the exercise of paternity and maternity in prison. This study examines the similarities and differences between parents deprived of liberty with respect to their paternal and maternal roles through semi-structured interviews with 294 inmates. We examined sociodemographic variables, criminal behavior, alcohol and/or drug use and treatment, mental health, institutionalization in child service and/or juvenile justice systems. Finally, the study examines how inmates perceive the exercise of their parental role. The results show the existence of a contradictory discourse regarding the meaning of being a good parent and how they exercise their role in prison. Their image of authority is affected because a family member is who generally is in charge of child care. The ways in which men and women exercise their role are different, but both groups face disjunctions regarding their parental role in prison, an aspect that must be addressed to prevent harm to their children.