As the health care model evolves to deliver on demand care, patients are becoming more responsible and interested in their data. The security of the medical devices and connected systems becomes increasingly more important because it plays a significant role in achieving better patient outcomes. Diabetes patients are at the forefront of this evolution and yet on the receiving end of diabetic equipment manufacturers delivering systems that support secure care. In order to deliver the best patient outcomes, complex trade-offs are required, including (1) usability, (2) cost, (3) time to market, (4) device life cycle, and (5) patient privacy. These trade-offs for security cannot be made without a comprehensive informed development process.