Technological advancements in wheelchairs, prosthetics and numerous other adaptive devices and practices have allowed injured or disabled athletes to compete in sport at all levels. These advancements will continue to improve athletic performance significantly both in para-sport and in Olympic sport. These biomedical and technological advancements also have the potential to change the very nature of sport itself. Those in sport management are often responsible for assessing and adapting the rules of sport to accommodate these advancements which are essential to maintaining the spirit of sport. This chapter provides background on the Paralympics and discussions on the need for rule changes pertaining to who is eligible to compete in the Paralympics should one rebuild their body – for instance, the reconstruction of a knee or elbow joint with stem cells that rejuvenate ligaments and tendons or the use of 3D printed titanium to replace bone. This chapter starts with the basic history of para-sport and the role of technology in its development. Next, the discussion moves to the rules of sport that support and maintain fairness with regard to technological advancements. This is followed by a dialogue on how technological advancements may challenge the spirit of sport with scenarios, followed by specific questions dealing with “the way forward” for managing cutting-edge technological advancements in sport. Through these questions, debate is encouraged regarding the acceptability/unacceptability of these technologies for use in para-sport.