Explore the intersection of cybersecurity and transportation systems in this 55-minute conference talk from Circle City Con 2016. Delve into Cyber Physical Systems (CPS) and their impact on safety, security, and privacy. Examine the concept of "wicked problems" and reasonable responses in the context of interconnected transportation networks. Learn about the NIST CPS Framework and its application to system-of-systems. Analyze the unique challenges and danger drivers associated with planes, trains, and automobiles in the age of increasing automation. Discover how seemingly benign technological advancements can inadvertently lead to the creation of potentially dangerous systems. Gain insights into semi-autonomous weapons systems and the future implications of interconnected transportation technologies. Conclude with a discussion on emerging trends and potential solutions for addressing the complex challenges posed by the Internet of Deadly Things.