Beyond Fixed Benchmarks and Worst-Case Attacks: Dynamic Boundary Evaluation for Language Models

Evaluation of large language models (LLMs) for safety, security, and privacy (SSP) relies heavily on static benchmarks, which suffer from score saturation, data contamination, and aggregation artifacts, and fail to capture sensitivity to linguistic variation. As a result, models that perform well on fixed test sets often fail under semantically equivalent rephrasings. We introduce SSP-Bench, a dynamic benchmarking framework that generates evaluation instances on demand while preserving domain consistency. The framework ensures label validity through externally grounded sources, enforces scope via service-specific validation, and calibrates difficulty using a multi-model steering panel. Benchmark construction is formulated as a multi-objective optimization problem over difficulty, separability, novelty, and diversity. Across 24 models and four SSP services, SSP-Bench reveals systematic failures of static evaluation, including near-zero correlation in safety rankings due to construct mixing, strong safety--over-refusal coupling, and hidden within-family regressions. These results show that static benchmarks can misrepresent model behavior, motivating dynamic, deployment-relevant evaluation.

Published evaluations of prompt-injection and jailbreak detectors for Large Language Models often suffer from two systematic weaknesses: per-dataset threshold tuning and undisclosed operating points. We describe an evaluation harness that addresses both. The detector under evaluation is scored across 16 public benchmarks (12,111 samples) using 5-fold cross-validation. StratifiedKFold (by row) is the headline pass; a parallel StratifiedGroupKFold pass over a composite key (parent-prompt id plus MinHash + LSH near-duplicate clusters at Jaccard $\gtrsim 0.8$) runs alongside it as a leakage-premium diagnostic. A single global operating point is selected on the held-out folds (max F1 subject to FPR $\leq 1\%$) and applied uniformly to every dataset, so per-dataset results reflect one threshold rather than per-benchmark optimisation. Generalisation is examined through a battery of diagnostics (leave-one-dataset-out cross-validation, a random-label control, adversarial validation, permutation feature importance, length-bias correlation, classifier-head agreement, cross-source near-duplicate detection, threshold transferability, train-vs-OOF agreement, and a paraphrase-invariance probe), most with a quantitative pass threshold and the remainder with a stated failure mode. For every external comparison, the detector's threshold is re-tuned to the competitor's published false-positive rate so head-to-head values are evaluated at matched operating points.

Benchmark datasets are central to evaluating Large Language Models (LLMs), yet they are typically conceived as monolithic tasks, obscuring substantial variation in the demands of individual samples. We introduce a dataset-centric meta-evaluation framework that audits benchmark datasets at the sample level along five latent dimensions: 1. Cognitive and Knowledge Demands, 2. Language and Content Quality, 3. Task Properties, 4. Context, and 5. Ethics, Safety, and Fairness. Applying this framework, we annotate five influential benchmarks -- MMLU, ARC, WinoGrande, HellaSwag, and TruthfulQA -- revealing pronounced internal heterogeneity that is not captured by aggregate accuracy scores. We show how these annotations enable criterion-driven orchestration of composite benchmark subsets across datasets, supporting targeted evaluation of model capabilities such as Reasoning Depth or Ethical Sensitivity. This approach reframes benchmark evaluation as dataset introspection, providing a principled methodology for analyzing and re-composing existing benchmarks to better reflect diverse evaluation needs.