A contact routing and scheduling system is provided allowing users to define various contact routing and scheduling contexts to direct a contact to a calendar of appointment availability representing the availability of a set of representatives pre-qualified to have times available for an appropriate appointment and to book an appointment as an integral part of the contact routing function. The system utilizes multiple visual user interfaces to allow users, contacts, and administrators to interact with the contact routing and appointment scheduling system. The system allows for user selection of contact routing and scheduling rules, association of scheduling activities to the contact routing process, and association of representatives who will ultimately accept appointments with contacts. The system also utilizes various techniques to associate contacts with particular contact routing and scheduling contexts received by the contact through email and/or other correspondence means.