Human-model alignment is critical for trustworthy AI-assisted decision-making systems. Yet, most work evaluates model predictions against single ground-truth labels, overlooking that humans themselves often disagree on labels, a signal of genuine ambiguity.

We investigate whether models struggle on the same instances that humans find difficult. We measure this on two vision datasets (FER+ and CIFAR-10H) where multiple human annotations per image capture human disagreement patterns.

We evaluate eight pretrained models across three architectures (ResNet, EfficientNet, MobileNetV3) in two parts: first, whether model uncertainty (softmax confidence, entropy) correlates with human disagreement, and second, whether predictive multiplicity measures (inter-model disagreement, Jensen-Shannon divergence) do. We find that it does not: alignment is weak in both dimensions.

At the discrete label level, 50.4% of CIFAR-10H images and 33.5% of FER+ images receive multiple valid classifications from humans, while the models converge on only one. These instances represent a critical failure case where humans perceive ambiguity and would request expert review, yet models decide confidently.

At the continuous score level, single-model uncertainty correlates weakly with human disagreement ($ρ= 0.24--0.55$), and predictive multiplicity provides only modest improvement. Widely-used uncertainty quantification methods do not reliably identify instances humans find ambiguous.

Model uncertainty should not be treated as a trustworthy signal by default for decision-making in high-stakes scenarios.