A system and method for identifying communication channels and appropriate timing of communications that facilitate enhancing or maximizing the utility of a communication between communicating parties, based on the participants' preferences and capabilities is provided. The system and method implement policies for facilitating optimal communications between communicating parties based on deterministic and/or uncertain preferences, capabilities and context, both present and predicted, where a decision to employ an initially selected channel and timing of communication may be overridden by contactor or contactee based on user-configurable triggers. The system and method further provide for mixed/multi-initiative overriding of the identified optimal communication channel and indicated best time for a communication. The methods can be implemented on a widescale communication system or within a single portable device. In one approach, the system attempts to optimize the inferred or directly accessed preferences of a contactee given the accessed or inferred preferences, capabilities and goals of the contactor while keeping the rationale and context of the contactee private. Such optimization can be achieved using preferences and policies concerning handling the attempted contact based on a deterministic specification or through inferring context, content and task under uncertainty by employing probabilistic or decision-theoretic inferences to attempt to maximize the expected utility of the communication to the contactee.