Volitional issues are important in today’s classrooms where autonomous students are expected to manage school demands on their own. A new kind of challenge has appeared with the advent of free Internet access in the classroom. Motivational conflicts may therefore arise between (1) immediate rewards of electronic chatting, surfing, and games and (2) the long-term rewards of academic achievement. Paradoxes of our educational system are emerging in the technology-rich classroom, for example, the basic need of student autonomy versus dealing with constraints to regulate one’s own behaviour. The main purposes of this article are, first, to discuss volitional issues on a theoretical level. Second, a field study is used to identify how students are using volitional (or self-discipline) strategies in technology-rich laissez-faire classrooms. Third, how schools may design institutional arrangements which can scaffold the student’s use of self-discipline strategies are discussed. The strategies which are enumerated may contribute to school programs that are to build self-discipline. Understanding how to design institutional features to influence students’ choices in directions that improve their academic achievement is one of the major challenges in education.