Many modern learning systems are used not to select a single best action, but to sample diverse high-quality outputs. Examples include entropy-regularized reinforcement learning, RLHF, and reward-guided generative modeling. Motivated by these settings, we study tilted sampling: an online learning problem in which the goal is to sample from the Gibbs distribution induced by an unknown reward function. We define sampling regret as the temperature-normalized cumulative KL divergence between the learner's distribution and the Gibbs target, corresponding to the suboptimality gap in entropy-regularized reward maximization. Our framework generalizes recent sampling-based and KL-regularized formulations in bandits and reinforcement learning. Our main contribution is a general regret framework that captures the different uncertainty structure of tilted sampling and classical regret minimization. While standard regret scales as $\widetilde{O}(\sqrt{T})$ due to first-order uncertainty, sampling regret is governed by squared confidence widths, yielding logarithmic-in-$T$ regret in standard settings at fixed temperature. We develop sampling analogues of UCB and Thompson sampling (UCS and TS$^2$) and provide unified regret decompositions that explain and extend recent logarithmic guarantees, including the first Bayesian sampling-regret decomposition based on new bounds for posterior-random Gibbs distributions. Our results show that learning to sample from a soft-optimal distribution is statistically distinct from learning to identify a hard optimum.

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