This paper seeks to call into question the meaning of «resocialization» in a socio-educational program for young offenders in Brazil known as «assisted freedom». We focus specifically on the process culminating in the judicial decision to put an end to probation. This decision is based on social workers' reports describing the youth's progress toward «resocialization». Through the analysis of social workers' discourses and written reports, we highlight the tension between social workers' values, their effective action potential and judicial expectations.