In the following article, the author discusses psychoeducational groups offered in a men’s maximum security prison by the Centre for Addiction and Mental Health’s (CAMH) Forensic Early Intervention Service (FEIS) in partnership with correctional services staff. The author shares observations and experiences facilitating mental health programs with clients in custody and explore related challenges, risks and opportunities. Outcomes and feedback from group participants are reviewed and recommendations for others interested in offering similar programs are presented.