A system and method for establishing a virtual private network (VPN) between a client and a private data communication network. An encrypted data communication session, such as a Secure Sockets Layer (SSL) data communication session, is established between a gateway and the client over a public data communication network. The gateway then sends a programming component to the client for automatic installation and execution thereon. The programming component operates to intercept communications from client applications destined for resources on the private data communication network and to send the intercepted communications to the gateway via the encrypted data communication session instead of to the resources on the private data communication network.