System and method for managing site-to-site VPNs of a cloud managed network

A management server includes a configuration and management module processing server configuration information, including a VPN peer list and VLAN/subnet settings. The management server automatically calculates the VPN configuration information, including the VPN peer subnet route information identifying which of the subnets participating in the VPN are behind which of the routers and keys to establish VPN tunnels between those routers participating in the VPN. Each of the routers participating in the VPN includes a VPN tunnel with the other routers participating in the VPN, a set of data structures storing data identifying contact information for each of the subnets participating in the VPN, a combination of an IP address and port to reach one of routers that that subnet is behind, and a forwarding module to forward traffic between the subnets.