Telemedicine services have been provided from Scotland for many years. Initial activities centred on the provision of health care to workers on the oil installations in the North Sea, to mixed-gas divers supporting the oil industry, and to scientific staff in British Antarctic Territory. Other Scottish research work has contributed to space medicine. The remote location of much of the Scottish population is currently the reason for much telemedicine research. This paper reviews the past quarter of a century of telemedicine in Scotland and identifies the principles that have led to success in some challenging locations. The same principles can be expected to apply when telemedicine services are provided more generally.