Adaptive prompt and program search makes LLM evaluation selection-sensitive. Once benchmark items are reused inside tuning, the observed winner's score need not estimate the fresh-data performance of the full tune-then-deploy procedure. We study inference for this procedure-level target under explicit tuning budgets. We propose SIREN, a selection-aware repeated-split reporting protocol that freezes the post-search shortlist, separates splitwise selection from held-out evaluation, and uses an item-level Gaussian multiplier bootstrap for uncertainty quantification. In a fixed-shortlist regime with smooth stabilized selection, the estimator admits a first-order item-level representation, and the bootstrap yields valid simultaneous inference on a finite budget grid. This supports confidence intervals for procedure-performance curves and pre-specified equal-budget and cross-budget comparisons. Controlled simulations and MMLU-Pro tuning experiments show that winner-based reporting can be optimistic and can change deployment conclusions, while SIREN remains close to the finite-sample reporting target.
Outliers are essential for evaluating and improving the robustness of machine learning systems, especially when future distributions may differ significantly from historical training data. In high-stakes applications, robustness often depends on rare cases that finite datasets fail to capture, making simple resampling or perturbation insufficient for stress scenario generation. Existing outlier synthesis methods typically rely on sparse neighborhoods, low support latent regions, or classifier boundary crossings, which can be heuristic, unstable, and tied to specific modalities or architectures. We therefore propose Sinkhorn Boundary Outlier Generation (SBOG), a structured framework for latent-space outlier generation that couples Sinkhorn optimal transport geometry with distributionally robust boundary modeling. The resulting Sinkhorn-induced support cost guides the sampler toward weakly supported boundary regions, while semantic constraints prevent uncontrolled drift from the intended context, yielding controlled deviations from the in-distribution reference measure rather than arbitrary sparse-region samples. Experiments on time series anomaly generation and image outlier synthesis show that our framework produces informative, semantically controlled outliers and improves downstream robustness evaluation across modalities, providing a foundation for stress scenario generation beyond empirical support.