Telemedicine involves linking primary care and specialty doctors with inmates at a different facility through video or other electronic media for selected medical consultations and other services, which eliminates the need to transport some inmates to an outside medical facility. To determine whether telemedicine is a worthwhile investment for a jail, three issues must be assessed: cost, quality of care, and security. Regarding cost, if the savings in transportation costs outweigh the cost of the telemedicine equipment and operation, then the facility realizes an economic benefit by investing in telemedicine. The impact of telemedicine on the quality of medical care depends in large measure on the level of services currently provided on- site, as well as on the policy decision regarding how to implement the system in relation to on-site staff. Telemedicine can positively impact the quality of medical care in a number of ways, including increased access to medical care, particularly at remote jails; increased access to medical specialists; more in-depth and more frequent follow-ups to prior treatment, faster diagnosis and treatment in some instances, and increased communications between on-site medical staff and other medical professionals regarding second opinions or other professional support. Regarding security, common wisdom indicates that a prisoner is most likely and most able to escape during those times that he/she is outside of secure facilities. There is thus an advantage from a security perspective in adopting technologies that eliminate the need to transport inmates to off-site locations. A detailed analysis of financial costs and benefits of telemedicine is presented. The data show that the benefits of telemedicine are tied closely to the raw number of inmates that can be seen, more than to other factors such as distances to medical facilities and transportation arrangements; therefore, urban jails can potentially achieve financial savings by implementing telemedicine, even if they are relatively close to hospitals. Future research is briefly discussed.