Systems and methods for establishing and conducting communication sessions augmented by contextual information. A call originator initiates a request to establish a communication session. The endpoint furnishes information identifying the call originator and intended call recipient(s). The method receives the request from the call originator and retrieves contextual information relating the call originator to the intended call recipient. If no contextual information has yet been derived, the contextual information is generated from data attributes available from one or more social networking sites. In some embodiments, the method generates the contextual information according to a set of rules and, if applicable, user preferences. The method handles the call request based on at least one of a set of rules, user preferences, and scheduling input received from the intended recipient responsive to receipt of the contextual information. The contextual information is accessible to some or all participants before and during the communication session.