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Legend has it, the first iteration of the Secure Sockets Layer (SSL) protocol was broken in ten minutes by Phillip Hallam-Baker and Alan Schiffman during a presentation by Marc Andreesen at MIT in 1994. In the following two decades the protocol has been improved and the implementations have been strengthened, but not without a steady stream of implementation vulnerabilities and protocol design errors. From the ciphersuite rollback attack to LogJam, SSL/TLS has seen a diverse set of problems.
From the HMAC-then-Encrypt vs Encrypt-then-HMAC debate to the preference for Cipher Block Chaining (CBC) modes, the 90s was an innocent time in secure protocol design. Daniel Bleichenbacher had not yet started his assault on RSA and the types of side-channel attacks that enabled BEAST and POODLE had not yet been discovered. Over the next two decades, not only were weaknesses revealed in the protocol, but implementation flaws were found in even the most widely deployed SSL/TLS libraries. By following the security-relevant changes in SSL/TLS over the years we can paint a picture of the hard lessons learned by the cryptographic community over the history of this protocol all and how we can prevent ourselves from repeating the mistakes of the past.