Is resocialize/resocialization an adequate notion/concept for tackling the penitentiary issue? This, in short, is the question that the text aims to answer. Result of qualitative research – using questionnaires and interviews – on the meanings attributed and perceived by different subjects and groups involved in the execution of custodial sentences, the discussion and analysis of the data uses references such as Eugenio Raúl Zaffaroni and Alessandro Baratta to tension the ambivalences and ambiguities that it encompasses. It suggests, in the end, that it should stop being used within the scope of Penal Services Policies and in the area of research on the penitentiary issue, given that its manageability of meanings entails both the invisibility of the relationships between social structure and punishment, and allows illusions of shared understandings which, in reality, mask divergent projects in relation to punishing and hold responsible in contemporary societies.