In the context of 7,637 high school students, the present study explored an hypothesized formulation of academic courage (defined as perseverance in the face of academic difficulty and fear) and its role in predicting academic performance (literacy and arithmetic) and various academic engagement measures (planning, task management, self-handicapping, disengagement, class participation, enjoyment of school, and positive academic intentions). Cluster analysis of core factors derived a four-group solution comprising courage, confidence, avoidance, and helpless orientations. Results from structural equation modeling demonstrated that courage and confidence are not significantly different on some academic measures (including performance) but that across the bulk of measures, confidence is more adaptive. However, courage was unambiguously more adaptive than avoidance and helpless orientations across all outcome measures. In summary, although confidence yields the most positive educational outcomes, courage can be considered an educationally effective response in the face or presence of fear. (Contains 1 figure and 4 tables.)