Data augmentation is a standard component of modern semantic segmentation pipelines, but most augmentation techniques allocate transformations uniformly across training samples or adapt to a single difficulty signal such as loss. This ignores the fact that segmentation difficulty is multi-factorial, since ambiguous predictions, persistent optimization errors, rare classes, and complex object boundaries can each make a sample informative in different ways. This paper introduces Difficulty-Aware Sample Allocation (DASA), an architecture-agnostic framework that assigns stronger augmentation to samples estimated to be more difficult. DASA combines prediction ambiguity, training loss, class rarity, and boundary complexity into a normalized difficulty score, then maps that score to sample-specific augmentation strength during iterative training. Experiments on Oxford-IIIT Pet and binary Pascal VOC segmentation with U-Net, DeepLabV3, and SegFormer-B0 show that DASA improves over standard training and is competitive with or stronger than single-signal adaptive baselines. On Oxford-IIIT Pet, DASA improves DeepLabV3 from 0.633 to 0.740 mIoU. On binary Pascal VOC, DASA obtains the best foreground IoU for all three evaluated architectures. These results attest to the value of multi-factor difficulty estimation as a practical mechanism for directing augmentation where it is most useful.

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