Distributionally Robust Optimization via Iterative Algorithms in Continuous Probability Spaces

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.

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.

Generative models are increasingly adopted in distributionally robust optimization (DRO), but existing approaches trade off model compatibility and adversarial structure: methods that accept arbitrary samplers do not restrict worst-case laws to a generator family, while generator-parameterized adversaries rely on model-specific access such as likelihoods, scores, or training data. We propose Generative Distributionally Robust Optimization (GDRO), a principled framework that accepts any sampleable conditional generator as the nominal model and restricts worst-case laws to a chosen conditional generator family. The key is the sampler-Sinkhorn pairing: samplers represent the conditional laws exactly, while Sinkhorn divergence compares their induced distributions without likelihood access and can be estimated from samples alone. The resulting population problem admits a direct finite-sample approximation and differentiable primal-dual implementation at the active decision context. For Lipschitz losses, the population Sinkhorn radius bounds downstream degradation. Across explicit and implicit generators, our method reduces rare-context inventory regret by 60% and SocialGAN navigation collisions by 50% relative to nominal decisions.