In 1999 the Greek Ministry of Justice decided to utilise telemedicine to improve health services in the largest prison in Greece (Korydallos Prison). The Nikea Hospital in Piraeus undertook to support the effort. For 12 months following installation, intensive “hands-on” training on the use of the system was offered to the staff of both the Korydallos Prison and the Nikea Hospital. However serious operational problems related either to prison bureaucracy or to the inflexibility the Greek National Health Service has annulled the effectiveness of the Korydallos Prison telemedicine system. Still, analysis of the system development history reveals that: (1) if freed from bureaucratic and labour related obstacles, prison telemedicine is a viable option. (2) Telemedicine can avert transfers to out-of-prison medical facilities. (3) 1f properly implemented, telemedicine can generate substantial savings and (4) telemedicine can greatly improve the quality of care available to prisoners.