The paper discusses the main stages of development of cryptographic protocols from SSL 2.0 (Secure Socket Layer) to TLS 1.3 (Transport Layer Security), which ensure the protection of transport layer data in the OSI model. A brief description of the modification of the RuTLS protocol based on TLS 1.3 and their main differences is given. The development of IPsec, which provides cryptographic protection of communications at the network level of the OSI model, is considered using examples of the development of the three most commonly used protocols. These include IKE (Internet Key Exchange), AH (Authentication Header), and ESP (Encapsulation Security Payload). For the SSL/TLS and IPsec specifications, the basic handshake protocols and the main stages of their development are considered. The described handshakes include primary cryptographic information exchange cycles in the form of identifiers of interaction participants, one-time numbers, lists of supported cryptographic combinations. Authentication of participants based on certificates, shared symmetric keys, data exchange for establishing a shared Diffie — Hellman secret, development of key material for secret keys of communication sessions, message authentication, and other cryptographic parameters are presented. For different versions of SSL/TLS and IPsec, the logical structures of application data cryptographic protection functions are described.