A routing system is provided for intelligent routing of instant messages between clients connected to a data network and customer service representatives connected to the network. The system comprises at least one instant message server and at least one intermediate server connected to and addressable on the network, the intermediate server capable of routing and accessible to the instant message server. Clients connecting to the instant message server through instant message software assert a connection link advertised by the instant message server to establish bi-directional communication between the client machine and the intermediate server. In preferred application, the intermediate server interacts with the client for identification of client and client software. The client request is then routed to an appropriate customer service representative running compatible software according to enterprise rules establishing an active instant message connection between the client and the selected customer service representative.