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Explore the complexities of HTTPS connections and data security in this 21-minute conference talk from USENIX Enigma 2016. Delve beyond the simple "lock" icon in web browsers to understand the intricate topology of services handling data after it leaves the HTTPS tunnel. Learn about the evolution of HTTPS termination, the impact of low-cost web infrastructure services on secure global caching, and the challenges of extending trust beyond the initial connection. Discover potential approaches to bridge security gaps and gain insights into the true journey of web data once it reaches the server side. Examine topics such as Moore's Law, cloud computing, modern web properties, edge networks, and negative security indicators to enhance your understanding of online data protection.