In one embodiment, a server and a client are configured to trust a certificate of an intermediate proxy device. The proxy device may then intercept a client-server security session request message sent from the client to the server. In response, the proxy device initiates a proxy-server security session with the server and obtains server security information from the server. Then, the proxy device initiates a client-proxy security session with the client using the trusted proxy certificate, and obtains client security information from the client. Upon obtaining the client security information, the proxy device creates a dynamic certificate using the obtained client security information and the trusted proxy certificate, and establishes the initiated proxy-server security session with the dynamic certificate. The proxy device then establishes the initiated client-proxy session, wherein the client-proxy security session and proxy-server security session transparently appear to the client and server as the requested client-server security session.