Play based systems, such as computer games, have proven effective as tools to enhance our human understanding, skills and capabilities in a number of real world activities. The active pursuit of gamification and applied games for tasks from education to design, training and simulation continues to grow. The field of healthcare is one key area offering significant potential. Raising the question of whether play based assistive tools, as a means to create greater understanding of serious medical conditions, and the health and lifestyle impacts they cause, can be effective. This research involved both the review of play based systems that are dedicated to assisting with diabetes, as well as the development of a new watch based mobile App designed specifically to assist players (both diabetic as well as broader community) in understanding the complex nature of managing diabetes. Diabetes is listed as the sixth leading cause of death worldwide and its improved management is listed as a priority by the world health organization. The results from the randomized control trial of the new watch based tool showed that participants who used the play based watch App, demonstrated a statistically significant improvement of their understanding of the condition and its management. This highlights the potential of play based digital tools to bring greater understanding of complex medical conditions to patients, care givers and the broader population.