Academic risk taking (selection of school-like tasks ranging in difficulty and probability of success) was examined in natural settings in an effort to identify influencing factors and to examine students’ intrinsic motivation. Six hundred two fourth-, sixth-, and eighth-grade Taiwan students from a rural and urban school were given a self-report measure of tolerance for school failure as well as a quantitative and spatial judgment risk-taking task with variable payoffs (response value increased with item difficulty). Level of response accuracy and level of item difficulty—with ability controlled—served as the risk-taking variables. As predicted, risk taking as defined by item difficulty increased with development. Also consistent with prediction, subjects obtained significantly lower accuracy scores (implying higher risk) on the less familiar spatial task than on the quantitative task. Failure tolerance decreased significantly with grade in the rural school only and was higher for boys than for girls. These results and other complex interactions are explained in terms of self-enhancement versus self-assessment goals, metacognitive skills, and psychological reactance. Suggestions for future research are also presented.