Optimized Certainty Equivalent Risk Minimization Using Samples: Algorithms, Convergence Rates, and Applications

We consider the optimization of the Optimized Certainty Equivalent (OCE) risk, with applications including portfolio optimization in finance, and uncertainty quantification, classification, and regression in machine learning. Our contributions cover popular special cases of OCE, such as entropic risk, mean-variance risk, and smooth variants of Conditional Value-at-Risk. Our treatment sets out the conditions that facilitate the extension of OCE to unbounded r.v.s.. We provide a useful characterization of OCE that links OCE to utility-based shortfall risk (UBSR). Our characterization enables us to form an OCE estimator from the classic sample-average approximation (SAA) of UBSR. We derive mean-squared error (MSE) bounds for our proposed OCE estimator. For OCE optimization, we first derive an expression for the OCE gradient using the characterization linking OCE to UBSR. This expression serves as the basis for a gradient estimator for the OCE. We derive non-asymptotic bounds on the MSE for the proposed OCE gradient estimator. We incorporate the aforementioned gradient estimator into a stochastic gradient (SG) algorithm to optimize OCE and quantify its convergence rate using non-asymptotic bounds that we derive. Finally, we present three experiments that use our OCE optimization algorithm to solve portfolio optimization and uncertainty quantification problems.

Optimizing Regret

Building on the identity that expected regret equals the covariance between costs and decisions, this paper develops the complete derivative theory of the covariance regret functional. We derive the Gâteaux derivative, showing that the universal steepest-descent direction is the contrarian policy $-(c-\bar{c})$, while ascent yields momentum. For linear policies $\hatπ(c) = Ac+b$, the gradient is the cost covariance matrix $Σ_c$, with a zero Hessian implying boundary-optimal solutions such as the minimum-variance portfolio. We extend to constrained optimization, sign-gradient duality between regret minimization and alpha maximization, finite-sample convergence bounds paralleling Thompson Sampling, and gradient-descent algorithms requiring only input observations, with applications to portfolio tilting and LLM-based allocation strategies.

Learning Predictive Ambiguity Sets for Decision-Focused Distributionally Robust Optimization

Predict-then-optimize systems usually compress uncertainty into a point forecast and then solve a downstream optimization problem as if the forecast were reliable. Distributionally robust optimization (DRO) offers protection against misspecification, but the ambiguity set is often centered at historical samples and uses a fixed radius. We propose \emph{learned predictive ambiguity sets} (LPAS): a deep contextual model outputs a finite nominal scenario distribution, a state-dependent Wasserstein radius, and optionally an anisotropic ground metric. These outputs define a contextual ambiguity set that feeds a DRO decision layer. The radius is trained by a combination of conditional quantile calibration, size regularization, and downstream decision loss, so that robustness is adaptive rather than globally fixed. We derive the finite dual form used by the decision layer, present a staged training algorithm, and evaluate the method on distributionally robust portfolio optimization with 20 S&P 500 constituents from 2018--2026. The proposed method substantially improves over equal-weight, predict-then-optimize, and historical Wasserstein DRO baselines, achieving 26.28% annualized return, Sharpe ratio 1.30, final wealth 1.61, and lower tail loss than a deep fixed-radius DRO baseline while using a smaller average radius. The results show that learned ambiguity radii can recover most of the performance of strong fixed-radius DRO while reducing unnecessary conservatism and improving regime adaptivity.

The Decision Geometry of Covariance Estimation for the Global Minimum-Variance Portfolio under Heavy Tails

The global minimum-variance portfolio (GMVP) is the canonical decision built from an estimated covariance matrix, yet covariance estimators are universally evaluated by matrix-norm loss, which is not the object the decision depends on. We characterise exactly how covariance-estimation error maps into GMVP suboptimality. We prove an exact regret identity and a non-asymptotic bound showing decision regret depends on the estimation error only through its action on the portfolio weights, scaled by portfolio concentration and the conditioning of the true covariance. From this we derive the decision geometry: GMVP regret is invariant to a (p-1)-dimensional projection of the p^2-dimensional error matrix, with invariance to the covariance-scale direction as an exact special case. We then apply the framework to heavy-tailed returns (tail index kappa in (2,4)), establishing the regret convergence rate implied by the centred operator-norm rate, and confirm the theory on a skew-t/t-copula simulation design with pre-registered analysis. The decision-focused advantage is a sharper constant and a concentration discount rather than a faster rate; we report an honest high-conditioning boundary of the rate prediction. The results complement recent decision-focused learning approaches by supplying the exact estimation geometry and consistency theory they lack.

Scaling Decision-Focused Learning to Large Problems with Lagrangian Decomposition

Decision-focused learning has shown great promise for addressing predict-then-optimize problems, particularly in the presence of under-specified models. However, its practical deployment is often hindered by high computational costs and limited scalability, as it requires solving a constrained optimization problem for each training instance at every iteration. To address these challenges, we propose a novel framework that incorporates Lagrangian decomposition into the decision-focused learning paradigm. Specifically, we introduce a new surrogate objective along with two loss functions for evaluating and training the underlying prediction model. We further propose two variants of our approach, which offer different trade-offs between computational efficiency and solution quality. Our framework can be seamlessly integrated with standard decision-focused learning methods, including Smart Predict-then-Optimize (SPO+) and Implicit Maximum Likelihood Estimation (IMLE). Through experiments on two standard benchmarks, the multi-dimensional knapsack problem and quadratic portfolio optimization, we demonstrate that our approach achieves competitive performance while remaining amenable to parallelization. In particular, it consistently outperforms traditional decision-focused learning methods on large-scale instances, involving up to eight times more variables than those typically considered in related work. The implementation is available at https://github.com/corail-research/DFL-LD.

Sampler-Robust Optimization under Generative Models

Modern stochastic optimization pipelines increasingly rely on learned generative models to represent uncertainty, while downstream decisions are evaluated almost entirely through Monte Carlo scenarios. This shifts the operational object of uncertainty from an explicit probability law to the sampler induced by the learned generator. Reliability therefore depends on two errors: sampler misspecification and finite-simulation error. We propose Sampler-Robust Optimization (SRO), which optimizes decisions against the worst-case sampler induced by perturbing the learned generator. This sampler-first formulation aligns with simulation-based decision pipelines and admits a sharpness-aware interpretation: it favors decisions whose performance is stable under generator perturbations, rather than merely under the nominal sampler. Under a coverage assumption, we show that the empirical worst-case objective provides a high-probability upper certificate for the true population objective, with finite-simulation error partially absorbed by the robustification used to guard against sampler misspecification. The framework accommodates generative models with or without explicit densities and admits efficient minimax procedures. Portfolio-optimization experiments show that SRO produces more stable decisions and improves out-of-sample performance under distribution shift.