Dermatology artificial intelligence (AI) models are predominantly trained on light-skinned, cancer-focused image collections, yet they are increasingly proposed for deployment in resource-constrained settings where patients differ from training populations along two confounded axes: skin tone and disease distribution. We investigate whether poor generalization is primarily caused by skin-tone underrepresentation or disease-distribution shift. We evaluate a cancer-trained baseline (ResNet-50 fine-tuned on HAM10000 and ISIC 2019), two dermatology foundation models (DermLIP and MONET), and a general-purpose vision model (DINOv3) as frozen feature extractors. Models are evaluated on a tone-stratified disease-matched dataset (Diverse Dermatology Images, DDI) and a disease-shifted tone-diverse dataset (Skin Condition Image Network, SCIN). Our results show that disease-distribution shift contributes more than skin tone in the evaluated settings. The cancer baseline decreases from 0.62 to 0.21 balanced accuracy when transferred to unfamiliar clinical conditions, while the within-disease skin-tone gap is smaller (0.10-0.18) and inconsistent. Label-free representation analysis shows that this failure reflects a representational limitation rather than only missing output labels: cancer-specialized features poorly cluster unfamiliar conditions (kNN purity lift +0.06 over chance), whereas dermatology-pretrained features retain stronger transferable structure (+0.23). Finally, we show that representation quality predicts recoverable performance under lightweight adaptation. Starting from dermatology foundation models, approximately ten labeled examples per clinical category recover most attainable performance. We release the evaluation protocol and code to support reproducible auditing of dermatology AI generalization.

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