Abstract: A communication system including a routing server and gateway server through which digital communication sessions are established along selected network routes based upon security requirements is disclosed. A digital communication request having a security level required is transmitted to a routing server. The routing server then determines a route, if available, having a route security rating sufficient for the specified communication and initiates the communication using the gateway server. The route security score is calculated based upon a table of security ratings associated with a plurality of connected networks segments which comprise a digital communication network.