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Explore the intricacies of cyber security through a captivating conference talk that delves into the vulnerabilities arising from innovative partnerships and integration of new technologies with existing security mechanisms. Discover a range of novel "Evil Maid" attacks on locked Windows machines, focusing on the high-profile collaboration between Microsoft's Cortana and Amazon's Alexa voice assistants. Follow the speakers' amusing journey of discovery and Microsoft's efforts to patch these vulnerabilities while minimizing public exposure. Gain insights into the challenges of combining new usage concepts with older security assumptions, the potential catastrophic outcomes of breaking these assumptions, and the crucial lessons for future integrations between AI technologies and IoT devices. Learn from the experiences of two accomplished cyber security experts: Amichai Shulman, a seasoned researcher, entrepreneur, and investor with 25 years of experience, and Yuval Ron, a Master's student at the Technion - Israel Institute of Technology and one of the youngest speakers at Black Hat USA 2018.