A method of enabling a proxy to participate in a secure communication between a client and a server. The method begins by establishing a first secure session between the client and the proxy. Upon verifying the first secure session, the method continues by establishing a second secure session between the client and the proxy. In the second secure session, the client requests the proxy to act as a conduit to the server. Thereafter, the client and the server negotiate a session master secret. Using the first secure session, this session master secret is then provided by the client to the proxy to enable the proxy to participate in secure communications between the client and the server. After receiving the session master secret, the proxy generates cryptographic information that enables it to provide a given service (e.g., transcoding, monitoring, encryption/decryption, caching, or the like) on the client's behalf and without the server's knowledge or participation. The first secure session is maintained between the client and the proxy during such communications.