Telemedicine has developed around certain assumptions about connectivity and format. From the pioneer work of Kenneth Bird in the 1970's medical events separated by distance were connected for videoconference interaction [1]. The connection implied well developed telecommunications tools at both ends of the interaction. Telemedicine in its most common manifestations relies upon electronic and professional familiarity plus training with proper technical support. This is true even with Internet telemedicine at the low end of bandwidth. A workable Internet service provider and intact telecommunication services are required at both ends. The assumption of intact, robust telecommunications fails when there is any significant disruption of services, power, or trained people to initiate a telemedicine request. The very nature of disasters whether made by nature, made by fellow humans or in war declarations implies a rupture of the social fabric, a failure of infrastructure. This loss of infrastructure and connection happens at a cruel time when the need for services in health matters is generally very much exacerbated. Extreme remote sites have never had infrastructure and therefore fit into this chapter. Is telemedicine incompatible with support and relief in disasters of remote places? Certainly not. However, telemedicine must adapt to the situation in ways not generally associated with standard telemedicine. New solutions can meet the expectation of being wherever services are need whenever the need arises. This chapter looks at the experiences, successes and failures of telemedicine in natural disaster, war, and extreme remote sites. The presentation is concluded with recommendations to make telemedicine integral to any disaster response and a natural tool for any human endeavor that requires sending people to remote and hostile environments.