Correctional education in Greece has been implemented since 1980’s. Second Chance Schools (SCS) in prisons were established in 2004, aiming at combating social exclusion. This study’s aim is to look into the reasons of school dropout and to interpret why inmates take part in the educational program provided by SCS, registering the motives, expectations and barriers. According to the findings, inmates dropped out particularly due to financial problems. They engage in the educational process having strong motives, primarily the beneficial calculation of the days of their sentence as well as it is a way to get out of the pains of imprisonment. Their expectations have to do with education, improvement of their vocational status, personal development and social acceptance. There were no barriers mentioned.