System and method for virtual private network network address translation propagation over nested connections with coincident local 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 the local gateway for an outer connection with a remote node and an inner connection with the same or a different remote node. Nested traffic received at the gateway on the outer connection is decapsulated and then source-in NATed. Traffic received at the gateway for transmission on the outer connection is first source-in NATed, and then encapsulated for communication on the outer connection.