The design of modern aerospace systems is commonly an exercise in creating and working with complex systems. This complexity stems from a combination of the complexity of the system itself, the interaction with environment that it operates in and often the organization which is creating the system. Historically, this complexity has been seen as a source of risk and uncertainty, especially with respect to future the future performance and utility of the system. Consequently actions were taken to minimize the downside risk, and especially eliminate what were considered significant failure modes. This risk minimization encompasses both technical and programmatic aspects. As a response the behavior of the program becomes inherently ‘stiff’ and is less likely to evolve to meet changes in the environment. Consequently it may actually be more likely that the program will fail suddenly and late in its development. One possible theory that helps to describe these behaviors and may unlock some of this information is Catastrophe Theory. When combined with a utility approach, specifically a Value-Driven approach this has the option to help organize the concept exploration and decision making phases of design.