Boundary delineation of anatomical structures in prostate MRI is often compromised by regional ambiguity. Automated segmentation methods relying on global overlap loss functions tend to be insensitive to surface deviations, leading to significant errors in ambiguous regions. Most existing uncertainty-aware methods treat uncertainty as a post-hoc quality indicator or prediction filter. We propose Contrastive Uncertainty Learning (CUL), a supervised framework that uses predictive uncertainty to directly guide representation learning. Using Monte Carlo Dropout, CUL identifies voxel-wise uncertainty and structures the embedding geometry accordingly: low-uncertainty, correctly predicted features form stable voxels while high-uncertainty or misclassified features are actively repelled, preventing feature collapse at difficult boundaries. We evaluate CUL on a 589-scan 3D prostate MRI multi-structure segmentation task (8 anatomical structures) using a ViT with UperNet decoder architecture. Average Dice ($83.38\%$) remains comparable to the baseline ($83.35\%$), while surface distance decreases significantly ($p<0.001$) across 6 of 8 anatomical structures. A hard-case analysis reveals a $22{\times}$ asymmetry between significantly improved and degraded cases ($18.8\%$ vs $0.9\%$). Ablation studies show that removing uncertainty-guided sample selection eliminates improvements for the transition zone, while replacing the contrastive objective with a boundary loss additionally removes bladder improvements, demonstrating that both uncertainty-guided sampling and the contrastive objective are essential for the observed gains. These findings demonstrate that the proposed uncertainty-guided representation learning is a useful mechanism for reducing the risk of extreme errors in safety-critical medical segmentation

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