Although the educational and psychological hazards of boredom are well documented, an increasing number of researchers have argued that boredom may be a helpful, rather than harmful, emotion for the growing individual. In this paper, we engage with this re-conception of boredom and explore its implications for contemporary education: Can boredom enhance student learning, or support certain forms of it? Can it be put to use in the classroom? What are the risks involved? In addressing these questions, we show that boredom can fulfil several important psychological functions under certain special conditions. At the same time, we argue that careful attention to the moral psychology of boredom reveals that it has significant disadvantages for helping students to develop a meaningful and fulfilling relationship to subject matter in the classroom. Against the backdrop of this analysis, we discuss the concept and experience of aspiration as a potential way of tempering and eventually obviating the psychological pitfalls of boredom. In the final section, we draw out several principles of an aspirational approach to grappling with boredom in education.