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Explore the complexities and challenges of encrypting Internet protocols in this 23-minute conference talk from USENIX Enigma 2016. Join Peter Eckersley and Yan Zhu from the Electronic Frontier Foundation as they delve into the unexpected intricacies of web encryption. Discover the "horror stories" encountered during their work on the Let's Encrypt and HTTPS Everywhere projects. Learn about the Byzantine nature of encrypting the Web, moving beyond the simple application of trapdoor one-way functions. Gain insights into new methods for maintaining safety and sanity in this complex digital landscape. The talk covers topics such as Lets Encrypt, web layers, and various security issues, providing a comprehensive look at the challenges faced in creating a secure encrypted web.