We examined how six gifted boys perceived the onset and development of their academic underachievement and what they identified as contributing aspects. Across the six boys' experiences, a similar pattern of onset and development of academic underachievement emerged. The boys discussed a lack of academic challenge, investment in hobbies, issues with time management and self-regulation, family transitions, and peer relations as contributing to the development of their academic underachievement. These aspects influenced the boys' value beliefs (e.g., not caring about grades) or maladaptive beliefs about themselves (e.g., lower self-worth), which in turn led to disengagement and underachievement.