This research investigates possible obstacles in the education of adolescents undergoing socioeducational measures in freedom in the city of Rio de Janeiro. Therefore, it was employed the empirical material collected in field research through participant observation and semi-structured interviews with professionals of Justice and Social Welfare, in addition to directors of schools that receive adolescents in conflict with the law. The study also included documentary analysis of information on 109 youths who have committed illegal acts and live in the downtown area. We tried to understand what happens at the interface between the school system, the judiciary and the social welfare system, the perceptions of the agents involved and the challenges of the relationship among them. The results show that a large part of the studied adolescents do not attend school. Those who study, in general, are allocated on flow correction projects or groups of Youth and Adult Education. As a rule, the measures in freedom are limited to bureaucratic referrals to school, employment agencies and the health posts. The school, which could serve as a link of integration among the agencies involved, seems smothered with structural problems such as the work overload of managers. According to the directors, adolescents in conflict with the law attend school, for a short time simply to comply with the determination of the judge. As a conclusion we discuss the need for building a network that will work in coordination to assure the rights of these young people, also providing support to school work and thus potentializing greater chances of interrupting the trajectory of law infraction practice and school failure.