The use of telepsychology, such as videoconferencing (VC) systems, has been rapidly increasing as a tool for the provision of mental health services to underserved clients in difficult to access settings. Inmates detained in restrictive housing appear to be at an increased risk of experiencing emotional and behavioral disturbances compared to their general population counterparts, yet they are less likely to receive appropriate treatment due to security constraints. The primary purpose of this article is to describe the process of implementing a novel telepsychology intervention specifically designed to offer group therapy to high-security, administratively segregated inmates. In addition, preliminary results on treatment and therapeutic process outcomes in a sample of 49 participants are reported. Although some evidence indicated that telepsychology was less preferred than in-person sessions, group differences on measures of psychological functioning and criminal thinking were not found across 3 conditions (telepsychology, in-person, and a no-treatment control). Furthermore, a number of limitations associated with program implementation and study design suggest that results be interpreted with caution and should not be used to discount the use of telepsychology as a viable treatment delivery option. Recommendations for future development and evaluation of telepsychological programs are discussed within the context of correctional settings and beyond.