The main purpose of this study is to present the practice, opportunities, and challenges of fine art education activities in a prison setting. Prison is primarily a form of punishment, a place where prisoners are disempowered and excluded from the outside world. Art is, therefore, extremely useful as it empowers prisoners and brings them contentedness and relaxation. In this research, we present a case study of Hungary and Slovenia. Through meaningful fine art education support activities, we can impact the awareness of the personal situation of prisoners and empower them to cope with various emotional and social challenges. By systematically incorporating fine art concepts, diverse and user-friendly fine art techniques, and content that can engage users where emotional and social skills are identified, strengthened, and indirectly reinforced, it is easier and better to endure the daily challenges of the prison environment. The presented fine art activities in prisons show that it would be useful to think in the direction of systematic involvement of artist teachers or students of fine art education within practical training to create a stimulating environment that helps to strengthen the affective, psychomotor, and cognitive development of juvenile and adult prisoners.