Deep learning models for crop damage assessment are typically trained and validated on curated public imagery, yet their behaviour when deployed in real orchards remains poorly quantified. This work measures and mitigates that gap for peach leaf damage classification, where climate-driven abiotic and biotic stresses produce visually similar foliar symptoms. A benchmark of 1366 manually annotated peach leaves covering six damage types was assembled from public sources, and a second, independently acquired dataset of 180 field images across four classes was collected in a commercial orchard as an unseen target domain. Eleven convolutional backbones and three attention-enhanced variants were compared; CBAM-EfficientNetB5 achieved the best source-domain performance (93.3\% accuracy, 0.849 macro F1). Applied directly to the target domain, source-trained models lost on average 0.21 macro F1 points (26.5\% relative), with 12 of 14 architectures degrading, confirming that benchmark performance substantially overestimates field behaviour. Three fine-tuning strategies were then evaluated as mitigation: feature extraction proved insufficient in nearly all cases, whereas full fine-tuning recovered performance, with CBAM-EfficientNetB3 reaching 0.9459 accuracy and 0.9297 macro F1 on the local domain. Attention mechanisms improved minority-class recall and adaptation efficiency, but did not by themselves confer robustness to domain shift. The results establish a transferability baseline for peach leaf diagnosis and quantify the adaptation cost of moving from public benchmarks to operational orchards.

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