The Internet's dynamic nature necessitates continuous evolution in web security technologies, such as Transport Layer Security (TLS) and emerging post-quantum cryptography (PQC). Cloudflare's Automatic SSL/TLS, launched during Birthday Week 2024, aims to automatically enhance encryption levels for domains by scanning and upgrading origin server configurations to the most secure modes possible. Over six million domains have benefited from this service, enhancing security without manual intervention. TLS 1.3 has accelerated secure connections through speculative key agreement guessing, while preparations for the quantum era involve hybrid key agreements integrating ML-KEM. Although early TLS versions suffered from vulnerabilities, subsequent iterations, particularly TLS 1.3, have streamlined encryption processes, boosting both security and performance. As encryption becomes increasingly integral, Cloudflare's Automatic SSL/TLS continues to facilitate a shift towards stronger encryption, helping domains transition from HTTP to HTTPS and preparing for the post-quantum era. Future enhancements aim to offer more visibility and control, ensuring a robust and encrypted Internet landscape.