Contextual optimization problems are prevalent in decision-making applications where historical data and contextual features are used to learn predictive models that inform optimal actions. However, practical applications often suffer from model misspecification due to incomplete knowledge of the underlying data-generating process, leading to suboptimal decisions. Existing approaches primarily address the well-specified case, leaving a critical gap in handling misspecified models. In this paper, we propose a novel Integrated Learning and Optimization (ILO) framework that explicitly accounts for model misspecification by introducing a tractable surrogate loss function with strong theoretical guarantees on generalizability, tractability, and optimality. Our surrogate loss aligns with the true decision performance objective, ensuring robustness to misspecification without imposing restrictive assumptions. The proposed approach effectively mitigates the challenges of non-convexity and non-smoothness in the target loss function, leading to efficient optimization procedures. We provide rigorous theoretical analysis and experimental validation, demonstrating superior performance compared to state-of-the-art methods. Our work offers a principled solution to the practically relevant challenge of model misspecification in contextual optimization.

We study the fundamental question of how informative a dataset is for solving a given decision-making task. In our setting, the dataset provides partial information about unknown parameters that influence task outcomes. Focusing on linear programs, we characterize when a dataset is sufficient to recover an optimal decision, given an uncertainty set on the cost vector. Our main contribution is a sharp geometric characterization that identifies the directions of the cost vector that matter for optimality, relative to the task constraints and uncertainty set. We further develop a practical algorithm that, for a given task, constructs a minimal or least-costly sufficient dataset. Our results reveal that small, well-chosen datasets can often fully determine optimal decisions---offering a principled foundation for task-aware data selection.