We study an extension of contextual stochastic linear optimization (CSLO) that, in contrast to most of the existing literature, involves inequality constraints that depend on uncertain parameters predicted by a machine learning model. To handle the constraint uncertainty, we use contextual uncertainty sets constructed via methods like conformal prediction. Given a contextual uncertainty set method, we introduce the "Smart Predict-then-Optimize with Robust Constraints" (SPO-RC) loss, a feasibility-sensitive adaptation of the SPO loss that measures decision error of predicted objective parameters. We also introduce a convex surrogate, SPO-RC+, and prove Fisher consistency with SPO-RC. To enhance performance, we train on truncated datasets where true constraint parameters lie within the uncertainty sets, and we correct the induced sample selection bias using importance reweighting techniques. Through experiments on fractional knapsack and alloy production problem instances, we demonstrate that SPO-RC+ effectively handles uncertainty in constraints and that combining truncation with importance reweighting can further improve performance.

We consider distributionally robust optimization (DRO) problems, reformulated as distributionally robust feasibility (DRF) problems, with multiple expectation constraints. We propose a generic stochastic first-order meta-algorithm, where the decision variables and uncertain distribution parameters are each updated separately by applying stochastic first-order methods. We then specialize our results to the case of using two specific versions of stochastic mirror descent (SMD): (i) a novel approximate version of SMD to update the decision variables, and (ii) the bandit mirror descent method to update the distribution parameters in the case of [Formula: see text]-divergence sets. For this specialization, we demonstrate that the total number of iterations is independent of the dimensions of the decision variables and distribution parameters. Moreover, the cost per iteration to update both sets of variables is nearly independent of the dimension of the distribution parameters, allowing for high-dimensional ambiguity sets. Furthermore, we show that the total number of iterations of our algorithm has a logarithmic dependence on the number of constraints. Experiments on logistic regression with fairness constraints, personalized parameter selection in a social network, and the multi-item newsvendor problem verify the theoretical results and show the usefulness of the algorithm, in particular when the dimension of the distribution parameters is large. History: Accepted by Antonio Frangioni, Area Editor for Design & Analysis of Algorithms—Continuous. Funding: This work was supported by the National Science Foundation [Grant 2112533]. Supplemental Material: The online appendix is available at https://doi.org/10.1287/ijoc.2023.0167 .