A communication system for automatically choosing a communication modality from a plurality of communication modalities for use for communication between distant communication entities is provided. The communication system includes a controller configured to: receive a message in the form of one of a first plurality of modalities from a message originator for transmission to a message recipient and select at least one modality for sending the message to the message recipient. To select the controller is configured to: determine the existence of any predetermined vehicle context requirements, predetermined static requirements, predetermined communication service provider requirements, communication context requirements, message recipient preferences, and message originator preferences; and make the selection based on those requirements and preferences. The controller is further configured to convert the received message to the selected modality and cause the message to be transmitted to the message recipient.