This chapter examines the implications of the paradoxical relationship, detailing how smart city technologies designed to produce urban resilience and reduce risks are actually opening up systems they are meant to augment to new forms of vulnerability and risk. Smart city technologies are no different, being afflicted with a range of security vulnerabilities and risks, and an ongoing struggle is evident between the cybersecurity industry and criminals and variously motivated hackers. Cyberattacks seek to “alter, disrupt, deceive, degrade, or destroy computer systems and networks or the information and/or programs resident in or transiting these systems or networks”. The market-led approach consists of commercial vendors developing smart city technologies taking a proactive, self-regulatory stance to security. Present strategies for addressing the vulnerabilities and risks posed by the mass adoption of networked technologies for city management are inadequate and predominantly rely on existing technical and training mitigation strategies and market-led solutions.