Classification models play a critical role in data-driven decision-making applications such as medical diagnosis, user profiling, recommendation systems, and default detection. Traditional performance metrics, such as accuracy, focus on overall error rates but fail to account for the confidence of incorrect predictions, thereby overlooking the risk of confident misjudgments. This risk is particularly significant in cost-sensitive and safety-critical domains like medical diagnosis and autonomous driving, where overconfident false predictions may cause severe consequences. To address this issue, we introduce the Fragility Index (FI), a novel metric that evaluates classification performance from a risk-averse perspective by explicitly capturing the tail risk of confident misjudgments. To enhance generalizability, we define FI within the robust satisficing (RS) framework, incorporating data uncertainty. We further develop a model training approach that optimizes FI while maintaining tractability for common loss functions. Specifically, we derive exact reformulations for cross-entropy loss, hinge-type loss, and Lipschitz loss, and extend the approach to deep learning models. Through synthetic experiments and real-world medical diagnosis tasks, we demonstrate that FI effectively identifies misjudgment risk and FI-based training improves model robustness and generalizability. Finally, we extend our framework to deep neural network training, further validating its effectiveness in enhancing deep learning models.