System and method for nesting virtual private networking connections with coincident endpoints

A communication network includes a plurality of nodes, selectively including a client, a remote gateway Internet service provider, the Internet, a local enterprise gateway, and an enterprise internal network. A local coincident endpoint is established at a first node for an outer connection with a remote node and an inner connection with a different remote node. The nodes participate in negotiations on the outer connection to set up the inner connection as a secure connection. Thereafter, responsive to communications on the inner connection, the first node establishes links to the outer connection selectively to receive or send communications double nested on the outer connection.