Bounded-Rationality, Hedging, and Generalization

Generalization bounds for deep learning models are typically vacuous, not computable or restricted to specific model classes. In this paper, we tackle these issues by providing new disagreement-based certificates for the gap between the true risk of any two predictors. We then bound the true risk of the predictor of interest via a surrogate model that enjoys tight generalization guarantees, and by evaluating our disagreement bound on an unlabeled dataset.We empirically demonstrate the tightness of the obtained certificates and showcase the versatility of the approach by training surrogate models leveraging three different frameworks: sample compression, model compression and PAC-Bayes theory. Importantly, such guarantees are achieved without modifying the target model, nor adapting the training procedure to the generalization framework.

Divergence-based regularization and Sharpness-Aware Minimization (SAM) are two prominent approaches for improving generalization in deep learning, both motivated by robustness to perturbations. However, their relationship has remained largely unexplored. Building on classical second-order expansions of $f$-divergences, we show that the two methods are locally consistent under parameter-space perturbations: both induce curvature-sensitive penalties, with divergence regularization yielding a Fisher-weighted quadratic form and SAM penalizing sharpness through the dominant Hessian eigenvalue. For negative log-likelihood objectives with exponential-family output distributions, this correspondence becomes especially transparent, since the Fisher and Gauss-Newton matrices coincide. We further show that the same local geometric perspective extends to input-space perturbations, where divergence-based regularization is defined through transformations of the input. In this setting, the regularizer induces a pullback quadratic form on the input space, providing a more general perturbation framework than standard SAM while preserving the same local sensitivity interpretation. To validate the analysis empirically, we use the asymmetric $α$-skew Jensen-Shannon divergence (JSD) family as a controlled testbed. Its local curvature coefficient scales as $α(1-α)$ and is maximized at the symmetric point $α=\tfrac12$, which recovers the standard JSD. Loss-landscape visualizations in the input-perturbation regime show that stronger induced curvature penalization is associated with flatter local minima. Experiments on four benchmark datasets further demonstrate that both accuracy and negative log-likelihood are consistently best near this regime of maximal curvature penalization.

Information theory plays a central role in establishing fundamental limits on what any learning or estimation algorithm can -- and cannot -- achieve, regardless of computational power. In this chapter, we provide an introduction to these connections. End-of-chapter exercises makes the material suitable for both classroom use and self-study. We begin by introducing concentration inequalities along with the notions of covering and packing in metric spaces, and the associated concept of metric entropy. These tools are essential for our analysis. We then introduce the learning-theoretic framework and derive upper bounds on generalization error in terms of metric entropy, Rademacher complexity, and the VC dimension, as well as mutual information and relative entropy. Finally we discuss the minimax estimation framework and establish lower bounds on minimax risk using Fano's inequality, yielding bounds in terms of relative entropy and covering and packing numbers. This manuscript contains preprint of a chapter under consideration for inclusion in the forthcoming third edition of Cover and Thomas's Elements of Information Theory, posted with permission from Wiley. It would follow the chapter posted at arXiv:2605.02989 . The table of contents of the new edition can be found at: https://docs.google.com/document/d/1L-m4oQEJw1PJhoxBeMwrrBD8S_HmvzMEkPbYvS24980/edit?usp=sharing . For feedback, please contact abbas@ee.stanford.edu.