Boiling the Frog: A Multi-Turn Benchmark for Agentic Safety

Background. Traditional safety benchmarks for language models evaluate generated text: whether a model outputs toxic language, reproduces bias, or follows harmful instructions. When models are deployed as agents, the safety-relevant object shifts from what the system says to what it does within an environment, and evaluating model responses under prompting is no longer sufficient to address the safety challenges posed by artificial intelligence. Recent developments have seen the rise of benchmarks that evaluate large language models as agents. We contribute to this strand of research. Approach. We introduce Boiling the Frog, a benchmark that evaluates whether tool-using AI models deployed in corporate and office settings are susceptible to incremental attacks. Each scenario begins with benign workspace edits and later introduces a risk-bearing request. The benchmark focuses on stateful multi-turn evaluation: chains expose a persistent workspace, place the risk-bearing payload at controlled positions in the turn sequence, and score whether the resulting artifact state becomes unsafe. Scenarios are organized through a three-level operational risk taxonomy grounded in the Boiling the Frog risks, the AI Act Annex I and Annex III high-risk contexts, and EU AI Act's Code of Practice on General-Purpose AI (GPAI). Results. Across a nine-model panel, aggregate strict attack success rate (ASR) is 44.4%. Model-level ASR ranges from 20.5% for Claude Haiku 4.5 to 92.9% for Gemini 3.1 Flash Lite, with Seed 2.0 Lite also above 80%. Average chain category-level ASR reaches 93.3% for Code of Practice loss-of-control scenarios.

Adversarial Humanities Benchmark: Results on Stylistic Robustness in Frontier Model Safety

The Adversarial Humanities Benchmark (AHB) evaluates whether model safety refusals survive a shift away from familiar harmful prompt forms. Starting from harmful tasks drawn from MLCommons AILuminate, the benchmark rewrites the same objectives through humanities-style transformations while preserving intent. This extends literature on Adversarial Poetry and Adversarial Tales from single jailbreak operators to a broader benchmark family of stylistic obfuscation and goal concealment. In the benchmark results reported here, the original attacks record 3.84% attack success rate (ASR), while transformed methods range from 36.8% to 65.0%, yielding 55.75% overall ASR across 31 frontier models. Under a European Union AI Act Code-of-Practice-inspired systemic-risk lens, Chemical, biological, radiological and nuclear (CBRN) is the highest bucket. Taken together, this lack of stylistic robustness suggests that current safety techniques suffer from weak generalization: deep understanding of 'non-maleficence' remains a central unresolved problem in frontier model safety.

Adversarial Poetry as a Universal Single-Turn Jailbreak Mechanism in Large Language Models

We present evidence that adversarial poetry functions as a universal single-turn jailbreak technique for large language models (LLMs). Across 25 frontier proprietary and open-weight models, curated poetic prompts yielded high attack-success rates (ASR), with some providers exceeding 90%. Mapping prompts to MLCommons and EU CoP risk taxonomies shows that poetic attacks transfer across CBRN, manipulation, cyber-offence, and loss-of-control domains. Converting 1,200 MLCommons harmful prompts into verse via a standardized meta-prompt produced ASRs up to 18 times higher than their prose baselines. Outputs are evaluated using an ensemble of open-weight judge models and a human-validated stratified subset (with double-annotations to measure agreement). Disagreements were manually resolved. Poetic framing achieved an average jailbreak success rate of 62% for hand-crafted poems and approximately 43% for meta-prompt conversions (compared to non-poetic baselines), substantially outperforming non-poetic baselines and revealing a systematic vulnerability across model families and safety training approaches. These findings demonstrate that stylistic variation alone can circumvent contemporary safety mechanisms, suggesting fundamental limitations in current alignment methods and evaluation protocols.