Aligning structured data is a fundamental problem in computer vision and machine learning, underlying tasks such as time series analysis, human action recognition, and visual representation learning. Existing alignment methods, including Dynamic Time Warping (DTW) and its differentiable variants, rely on deterministic similarity measures and are therefore sensitive to heterogeneous and noisy features. In this work, we introduce uncertainty-aware alignment, a probabilistic framework that models pairwise correspondences with heteroscedastic uncertainty and performs structured matching along alignment paths. Our formulation, uncertainty-DTW (uDTW), assigns each correspondence a Normal distribution and parametrizes each alignment path by a Maximum Likelihood Estimate objective consisting of (i) a precision-weighted matching term that suppresses unreliable features, and (ii) a log-variance regularization that prevents degenerate solutions. This yields a probabilistic alignment mechanism that is robust to noise and interpretable, as uncertainty directly reflects the reliability of matches. We further generalize this framework from temporal sequences to tokenized visual representations, enabling structured matching over sets of visual tokens. The learned uncertainty can be interpreted as a reverse-attention: semantically relevant regions exhibit low uncertainty and dominate the alignment, while ambiguous/noisy regions have high uncertainty. This provides a connection between alignment, attention, and uncertainty modeling. We evaluate the proposed framework across diverse domains. The results demonstrate consistent improvements over state-of-the-art methods and show that learned uncertainty correlates with semantic importance. These findings establish uncertainty-aware alignment as a general, robust, and interpretable framework for learning from structured data.