The purpose of the present paper is to investigate educators’ perceptions regarding the evaluation of the institution of Second Chance Schools in Greece (SCS) that also operate inside correctional centers (SCSCC). Second chance education is a European programme within the framework of fighting against social exclusion that aims at early school leavers and adult prisoners, who have not completed the compulsory secondary education. A cross-national survey was carried out using a self-reported questionnaire with 367 participants that work in SCS and SCSCC. The outcomes of the study reveal that SCS and SCSCC educators can recognize the ‘curriculum’, the ‘infrastructure’ and the ‘opportunities of socioeconomic integration’ as major factors of SCS evaluation. The educators are generally satisfied with the curriculum and the opportunities of socioeconomic integration provided and have a neutral opinion about infrastructure. According to the findings, infrastructure is evaluated better in SCS located in continental Greece compared to insular located SCS and curriculum is better evaluated by principals and teachers who had completed postgraduate studies. However, teachers working in SCSCC were less satisfied with the opportunities of socioeconomic integration compared to teachers working in SCS.