I will present research exploring the use of representations of probability and utility in human--computer interaction. Key concepts and challenges will be introduced in the context of several efforts at Microsoft Research, including the Lumiere and Lookout projects. Lumiere research centers on developing methods and architectures for inferring a user's goals and needs by considering an ongoing stream of user actions. Lookout focuses on an exploration of mixed-initiative user interfaces--interfaces that are designed with the assumption that people and automated services will collaborate to achieve goals. I will conclude by presenting highlights of research on the foundations of human--computer dialogue, taking the perspective of interaction as decision making under uncertainty.