Interactions between instructors and students at distance learning universities are crucial in motivating students and enhancing learning outcomes. Although prior empirical studies have examined email messages at distance learning universities from different perspectives, this is the first study, to the best of our knowledge, to explore the effectiveness of emails considering the students' profiles and their behavior on learning platforms. Specifically, we differentiate between students who are "active" in virtual courses (called "active" students) and students who are "nonactive' in virtual courses (called "inactive" students) in order to design email content and motivate students. Focusing on this differentiation and a control group, we investigate in a Managerial Accounting for Tourism course the effectiveness of motivational emails to: (1) engage students in the virtual course; (2) detect similar behaviors according to sociodemographic characteristics; and (3) affect learning outcomes.