This chapter introduces context-aware computer-mediated communication for distance learning systems. It argues that linking deeply communication to learning activities offers an interesting approach to develop the efficiency of systems in facilitating and increasing discussions between learners. To make this link, the author bases his work on various theories, such as communication theories, situated cognition theory, and activity theory. This theoretical study leads to research issues concerning a contextual forum model. The description of the computing implementation of this model aims at giving researchers some possible uses and recommendations in dealing with context-sensitive communication tools. Finally, the chapter mentions futures trends and suggests emerging research opportunities within the field of communication services that are able to adapt dynamically to the user’s activity.