Learning Predictive Ambiguity Sets for Decision-Focused Distributionally Robust Optimization

Distributionally robust optimization (DRO) is widely used for decision-making under uncertainty, but its adversarial focus on worst-case loss can lead to overly conservative policies. To mitigate this, we study ex-ante Distributionally Robust Regret Optimization (DRRO) with Wasserstein ambiguity sets, designed to balance robustness with upside potential. We develop a theory of Wasserstein DRRO (WDRRO) paralleling Wasserstein DRO. Under smoothness and regularity, WDRRO selects among ERM optima by a first-order gradient-discrepancy rule. If the ERM optimizer is unique, first-order sensitivity vanishes and a second-order expansion governs deviations. For convex quadratics ERM and DRRO coincide for any radius. We then study regimes where these assumptions fail: nondifferentiable max-affine losses, discrete references, and larger radii, where WDRRO can differ from ERM and WDRO. We show that computing WDRRO regret is NP-hard even without bilinear terms. Nevertheless, we develop exact algorithms, a tractable convex relaxation with guarantees, and experiments showing tightness and loss-dependent behavior.

Uncertainty quantification from finite data is central to machine learning, optimization, and automation systems, where decisions must remain reliable under limited samples and test-time distribution shift. Conformal prediction (CP) and distributionally robust optimization (DRO) offer two complementary approaches: CP constructs data-dependent prediction sets with distribution-free finite-sample validity under exchangeability, while DRO optimizes worst-case performance over an ambiguity set around an empirical distribution. We develop a unified probabilistic perspective on CP and DRO by viewing both as ways to turn finite calibration data into a data-dependent quantile estimator that a test score falls below with high probability. From this perspective, CP and DRO correct the empirical quantile along two coordinates of the same family of estimators: CP inflates the quantile level, whereas DRO shifts the quantile value through an ambiguity radius. Both methods provide the same calibration-conditional guarantee for the true distribution, requiring the target coverage to hold with high probability over the calibration sample. Their constructions differ, however: CP uses a closed-form, distribution-free level correction, while DRO uses a value-space correction whose certified radius depends on properties of the unknown distribution and additionally guarantees coverage uniformly over the ambiguity set. This distinction emerges in the tails of the score distribution. Because CP relies on sparse upper-tail order statistics of the calibration samples, its level inflation barely moves the estimator when those samples are dense near the target quantile but overshoots when they are sparse, whereas a well-chosen DRO radius corrects in value space and may avoid this overshoot.

We propose a distributionally robust approach to learning hyperparameters for first-order methods in convex optimization. Given a dataset of problem instances, we minimize a Wasserstein distributionally robust version of the performance estimation problem (PEP) over algorithm parameters such as step sizes. Our framework unifies two extremes: as the robustness radius vanishes, we recover classical learning to optimize (L2O); as it grows, we recover worst-case optimal algorithm design via PEP. We solve the resulting problem with stochastic gradient descent, differentiating through the solution of an inner semidefinite program at each step. We prove high-probability bounds showing that the true risk of the learned algorithm is at most the in-sample L2O optimum plus a slack that shrinks with the sample size, and is no worse than the worst-case PEP bound. On unconstrained quadratic minimization, LASSO, and linear programming benchmarks, our learned algorithms achieve strong out-of-sample performance with certifiable robustness, outperforming both worst-case optimal and vanilla L2O baselines.