Abstract Intelligent Tutoring Systems (ITS) is the interdisciplinary field that investigates how to devise educational systems that provide instruction tailored to the needs of individual learners, as many good teachers do. Research in this field has successfully delivered techniques and systems that provide adaptive support for student problem solving in a variety of domains. There are, however, other educational activities that can benefit from individualized computer-based support, such as studying examples, exploring interactive simulations and playing educational games. Providing individualized support for these activities poses unique challenges, because it requires an ITS that can model and adapt to student behaviors, skills and mental states often not as structured and welldefined as those involved in traditional problem solving. This paper presents a variety of projects that illustrate some of these challenges, our proposed solutions, and future opportunities.