The present text consists of a proposal of theoretical-political elaboration about the experiences lived by adolescents who are subjected to socio-educational measures that entail deprivation of freedom. It is the result of a research based on Historical-Cultural Psychology, from the rescue of its philosophical and epistemological roots, in the scope of dialectical historical materialism.The objective was to investigate, from the narratives of adolescent-inmates, the relationship between criminalization and schooling in their developmental trajectories. More specifically, it aimed to: a) analyze, from the perspective of the adolescents, the social dimensions of what criminalization constitutes; b) identify the production of meanings of the processes of schooling in the trajectory of those adolescents; c) analyze the facets of the process of institutionalization that, during the fulfillment of the socio-educational measure, are related to the process of criminalization. To achieve these objectives, a four-month study was carried out within a school that exists inside a Youth Detention Center in the Brazilian Federal District (with a class of twelve students of the first year of high school). Participatory methodologies were used, which mediated debates about the processes of both criminalization and schooling that were experienced by adolescents. From the narratives that emerged during the meetings, we present three axis of analysis in the themes of criminalization, schooling and socioeducational system. These are distinct concepts, approached in different ways by the various theoretical perspectives (that exist in Psychology and also outside of it), but which are found and materialized in the experience of the subjects in this study as dialectical components of a same totality. The results showed that the criminalization that crosses the experience of adolescents deprived of their liberty, inside and outside the Youth Detention Center, maintains a close relationship with the inefficacy of the schooling processes experienced by them. As developments, we present some premises that deserve to be considered when the focus of 12 analysis is the experience of adolescents deprived of their liberty, namely: a) deprivation of liberty is incompatible with the proposal of a transformative education; b) the consolidation of a school education project with a view to social transformation is urgent; c) political emancipation is essential to the formation of self-consciousness; d) the end of the criminalization of poor youth is impossible without overcoming class society.