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Explore the vulnerabilities and security challenges of urban infrastructure in this Black Hat conference talk. Delve into a comprehensive methodology for reverse engineering cities and identifying their attack surfaces. Examine proven hacking capabilities and known threats from criminal and nation-state actors applicable to city-level attacks. Learn strategies for penetration testing to highlight and mitigate vulnerabilities at the urban scale. Discover complementary approaches including exercises, collective training, metrics, and specialized attack/defend ranges. Gain insights into securing cities as a crucial step towards national cybersecurity, while acquiring practical tools and techniques to improve urban information security. Understand the complex interdependencies between agencies, infrastructure, and various levels of government that make securing cities a unique challenge.