Communication of emotion is of fundamental importance to the performance of music. However, recent research indicates that expressive aspects of performance are neglected in music education, with teachers spending more time and effort on technical aspects. Moreover, traditional strategies for teaching expressivity rarely provide informative feedback to the performer. In this chapter we explore the nature of expressivity in music performance and evaluate novel methods for teaching expressivity based on recent advances in musical science, psychology, technology, and acoustics. First, we provide a critical discussion of traditional views on expressivity, and dispel some of the myths that surround the concept of expressivity. Then, we propose a revised view of expressivity based on modern research. Finally, a new and empirically based approach to learning expressivity termed cognitive feedback is described and evaluated. The goal of cognitive feedback is to allow the performer to compare a model of his or her playing to an “optimal” model based on listeners’ judgments of expressivity. This method is being implemented in user-friendly software, which is evaluated in collaboration with musicians and music teachers.