Disproving the Feasibility of Learned Confidence Calibration Under Binary Supervision: An Information-Theoretic Impossibility

We prove a fundamental impossibility theorem: neural networks cannot simultaneously learn well-calibrated confidence estimates with meaningful diversity when trained using binary correct/incorrect supervision. Through rigorous mathematical analysis and comprehensive empirical evaluation spanning negative reward training, symmetric loss functions, and post-hoc calibration methods, we demonstrate this is an information-theoretic constraint, not a methodological failure. Our experiments reveal universal failure patterns: negative rewards produce extreme underconfidence (ECE greater than 0.8) while destroying confidence diversity (std less than 0.05), symmetric losses fail to escape binary signal averaging, and post-hoc methods achieve calibration (ECE less than 0.02) only by compressing the confidence distribution. We formalize this as an underspecified mapping problem where binary signals cannot distinguish between different confidence levels for correct predictions: a 60 percent confident correct answer receives identical supervision to a 90 percent confident one. Crucially, our real-world validation shows 100 percent failure rate for all training methods across MNIST, Fashion-MNIST, and CIFAR-10, while post-hoc calibration's 33 percent success rate paradoxically confirms our theorem by achieving calibration through transformation rather than learning. This impossibility directly explains neural network hallucinations and establishes why post-hoc calibration is mathematically necessary, not merely convenient. We propose novel supervision paradigms using ensemble disagreement and adaptive multi-agent learning that could overcome these fundamental limitations without requiring human confidence annotations.