Although self-initiative is recognized as instrumental to success in college, some students do not take responsibility for their academic development and fail to make the transition from high school to college. This problem is exacerbated when bright, highly skilled students drop courses or quit college entirely. Research into this paradox of failure reveals that, although high academic control benefits learning-related emotions, cognitions, motivation, and performance, it is not sufficient to ensure optimal success. Along with academic control other factors are implicated in the paradox. In this 3-year longitudinal study, four groups of students who differed in academic control (low, high) and failure preoccupation (low, high) were tracked using broad indices of scholastic development. Overall, students higher in academic control obtained better 3-year GPAs and withdrew from fewer courses. More notable, however, high-academic-control students who were concerned about failure had better 3-year GPAs and also were less likely to withdraw from courses or quit university than the other three groups. Paradoxically, high-academic-control students who were less concerned about failure did poorly. In qualifying the assumption that more perceived control is always better, these results are interpreted following social cognition theory.