A system and method for identifying ideal channels for communications based on an analysis of communication channel reliability, communicating party preferences, and communicating party contexts is provided. The system attempts to optimize the utility of a communication based on inferred or directly accessed channel reliability data, communicating party preferences and communicating party contexts. Such optimization can be achieved using reliabilities, preferences and policies concerning handling the attempted contact based on a deterministic specification or through inferring reliability, context, content and task under uncertainty by employing decision-theoretic inferences. The methods may consider channels currently available as well as channels available at later times. Thus, the service can include automated rescheduling of communications based on a consideration of forecasts of reliability and availability. The approach may include the use of forecasts about the time required for a communication and the likelihood that a connection will be dropped or will lose fidelity over this period of time. The methods may also include a consideration of metadata within a standard schema that is transmitted along with a communication attempt, the metadata representing information about attributes like the potential communication channels, the identity of the contactor, the task at hand, and the context of the communicating parties. The invocation of the communication service may be performed in a variety of ways, including single button invocations, and via a communication service that is more deeply integrated with other applications and functionalities.