Explore two decades of web cryptography evolution in this 47-minute conference talk from linux.conf.au 2019. Delve into the challenges of suboptimal configuration and the persistence of outdated encryption algorithms, digests, and protocols. Learn about the current transitions in web security, including TLS, cipher suites, HTTP security headers, and certificate authorities. Discover the implications of moving towards an encrypted-by-default web and the importance of dropping legacy support to enhance security. Gain insights into optimizing web security configurations for modern browsers and staying compliant with current standards.