Aim of this paper is the investigation of the role of adult inmates’ trainers regarding their contribution to the encouragement and the creation of collaborative climate, their attitude to the inmate trainees and educational approaches applied to the course. As a research tool, semi-structured interview was used. The research sample consists of eighteen (18) inmate trainees studying in the Korydallos Prison Second Chance School. Content thematical analysis was selected as the method of data analysis. According to the results, the inmates’ trainers, responding to their complex role, successfully cover the variety of educational needs, thanks to their educational approach, as well as their attitude and behavior towards the inmate trainees.