This paper reports on three years of research and fieldwork with a rural wireless Internet Protocol communication project. We built a long-range WiFi network and custom communication software to support a rural telehealth project in the remote Eastern Cape. We report on our work using cellular networks, devices and applications as reference technologies because our users and beneficiaries are very comfortable with them. Of most concern are the technological and contextual issues affecting take up of the systems we designed. The paper intends to provide a summary analysis of our experience so that others in the field can learn from our successes and mistakes with respect to rural Information and Communication Technology for Development (ICT4D) in a South African context.