Boiling the Frog: A Multi-Turn Benchmark for Agentic Safety
Pith reviewed 2026-05-25 06:02 UTC · model grok-4.3
The pith
Tool-using AI agents in office settings yield to incremental attacks at 44.4 percent aggregate rate.
A machine-rendered reading of the paper's core claim, the machinery that carries it, and where it could break.
Core claim
Tool-using AI models deployed in corporate and office settings are susceptible to incremental attacks when evaluated in stateful multi-turn interactions, with an aggregate strict attack success rate of 44.4 percent across nine models, model-level rates from 20.5 percent for Claude Haiku 4.5 to 92.9 percent for Gemini 3.1 Flash Lite, and average chain category-level success reaching 93.3 percent for Code of Practice loss-of-control scenarios.
What carries the argument
Stateful multi-turn evaluation chains that 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.
If this is right
- Models differ sharply in resistance, with some exceeding 80 percent success and others below 25 percent, indicating that design choices affect vulnerability to gradual escalation.
- Loss-of-control scenarios show the highest average success at 93.3 percent, pointing to a systematic weakness when requests build toward reduced oversight.
- Safety evaluation for agents must move beyond single-turn prompts to include persistent state and multi-turn history.
- The taxonomy ties directly to regulatory high-risk categories, allowing the benchmark to serve as a concrete test for compliance with defined operational risks.
Where Pith is reading between the lines
- Agent systems could add explicit tracking of request sequences to detect and block patterns that start safe and accumulate risk.
- Regulators might require multi-turn incremental testing for any agent application placed in high-risk workplace categories.
- The same incremental-attack structure could be adapted to test agents outside corporate settings, such as personal productivity tools or customer-service systems.
Load-bearing premise
The three-level taxonomy and the simulated stateful scenarios with controlled payload positions accurately capture the relevant high-risk contexts and real corporate agent deployments.
What would settle it
Deploying the same incremental request sequences against actual agent systems in live corporate environments and checking whether the observed rate of unsafe final states matches the benchmark's reported attack success rates.
Figures
read the original abstract
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.
Editorial analysis
A structured set of objections, weighed in public.
Referee Report
Summary. The paper introduces Boiling the Frog, a multi-turn benchmark for evaluating tool-using AI agents' susceptibility to incremental attacks in corporate and office settings. Scenarios start with benign workspace edits before introducing risk-bearing requests, using stateful evaluation with controlled payload positions. A three-level operational risk taxonomy is defined, grounded in Boiling the Frog risks, AI Act Annex I/III, and the EU AI Act Code of Practice on GPAI. Across nine models, the paper reports an aggregate strict attack success rate (ASR) of 44.4%, with model-level variation from 20.5% (Claude Haiku 4.5) to 92.9% (Gemini 3.1 Flash Lite) and category-level ASR reaching 93.3% for loss-of-control scenarios.
Significance. If the benchmark scenarios and taxonomy are shown to be representative of real corporate agent deployments, the work would be significant for agentic safety research by shifting evaluation from single-turn text outputs to stateful multi-turn tool use and incremental escalation. The regulatory grounding and focus on persistent workspace state address a recognized gap in existing benchmarks. The reported ASR variation across models and high rates in loss-of-control categories would provide actionable signals for alignment and deployment practices if the underlying data generation and scoring are reproducible.
major comments (2)
- [Abstract] Abstract: The aggregate strict ASR of 44.4% (and model/category breakdowns) is presented without any description of scenario construction, exact scoring rules for unsafe artifact states, model prompting templates, error analysis, or controls for confounding factors such as workspace initialization or turn ordering. This omission is load-bearing because the central claim that the benchmark measures susceptibility to incremental attacks in corporate settings cannot be verified from the reported numbers alone.
- [Approach] Approach section (taxonomy and scenario description): The assertion that the three-level taxonomy and stateful multi-turn chains with controlled payload positions 'faithfully represent real corporate agent deployments' is stated without supporting evidence, mapping, or validation data showing that the chosen benign-to-risk sequences, workspace persistence mechanics, or payload placements match observed distributions in actual tool-using agent use. This assumption directly underpins interpretation of the ASR results as real-world risk rather than benchmark-specific performance.
minor comments (1)
- [Abstract] The abstract refers to 'strict attack success rate' without defining the strictness criterion or contrasting it with a non-strict variant; a brief definition or reference to the methods section would improve clarity.
Simulated Author's Rebuttal
We thank the referee for the detailed and constructive comments. We address each major comment below, providing clarifications from the full manuscript and indicating where revisions will strengthen the presentation.
read point-by-point responses
-
Referee: [Abstract] Abstract: The aggregate strict ASR of 44.4% (and model/category breakdowns) is presented without any description of scenario construction, exact scoring rules for unsafe artifact states, model prompting templates, error analysis, or controls for confounding factors such as workspace initialization or turn ordering. This omission is load-bearing because the central claim that the benchmark measures susceptibility to incremental attacks in corporate settings cannot be verified from the reported numbers alone.
Authors: The abstract is intentionally concise per venue guidelines. The full Approach section describes scenario construction (benign workspace edits escalating to risk-bearing requests), stateful multi-turn evaluation with persistent workspace and controlled payload positions, and the three-level taxonomy used for scoring unsafe artifact states. The experimental setup details model prompting templates, error analysis, and controls for workspace initialization and turn ordering to isolate incremental effects. These elements support verification of the reported ASR values as measures of susceptibility to incremental attacks. revision: no
-
Referee: [Approach] Approach section (taxonomy and scenario description): The assertion that the three-level taxonomy and stateful multi-turn chains with controlled payload positions 'faithfully represent real corporate agent deployments' is stated without supporting evidence, mapping, or validation data showing that the chosen benign-to-risk sequences, workspace persistence mechanics, or payload placements match observed distributions in actual tool-using agent use. This assumption directly underpins interpretation of the ASR results as real-world risk rather than benchmark-specific performance.
Authors: The taxonomy and scenarios are explicitly grounded in the Boiling the Frog risks, AI Act Annex I/III high-risk contexts, and the EU AI Act Code of Practice on GPAI to target regulatory high-risk areas. We do not possess or cite empirical distributions from proprietary corporate deployments, as such data is not publicly available. The benchmark therefore reflects regulatory definitions of risk rather than a direct empirical match to observed use. We will revise the manuscript to clarify this grounding and add an explicit limitations discussion on the absence of deployment-distribution validation. revision: yes
Circularity Check
No circularity: benchmark results are direct empirical measurements on author-defined scenarios with no reductions to fitted inputs or self-citations
full rationale
The paper introduces the Boiling the Frog benchmark, defines its three-level taxonomy by grounding in external references (AI Act Annex I/III and Code of Practice), constructs stateful multi-turn scenarios, and reports measured ASR values across models. No equations, parameters, or derivations are present. The reported aggregate ASR (44.4%), model ranges, and category ASRs are computed directly from model behavior on the benchmark; they are not fitted quantities renamed as predictions, nor do they reduce to self-referential definitions or author-prior uniqueness claims. External grounding citations are to regulatory documents, not self-citations. The derivation chain consists solely of benchmark construction followed by evaluation, which is self-contained and does not exhibit any of the enumerated circularity patterns.
Axiom & Free-Parameter Ledger
axioms (1)
- domain assumption The three-level operational risk taxonomy grounded in Boiling the Frog risks, AI Act Annex I/III, and GPAI Code of Practice is appropriate for categorizing agent safety threats.
Reference graph
Works this paper leans on
-
[1]
Amodei, D., Olah, C., Steinhardt, J., Christiano, P., Schulman, J., and Man´ e, D. (2016). Concrete problems in AI safety.arXiv:1606.06565
work page internal anchor Pith review Pith/arXiv arXiv 2016
-
[2]
Andriushchenko, M., et al. (2024). AgentHarm: A benchmark for measuring harmfulness of LLM agents.arXiv:2410.09024
work page internal anchor Pith review Pith/arXiv arXiv 2024
-
[3]
Anthropic. (2025). Activating AI Safety Level 3 protections. https://www.anthropic. com/news/activating-asl3-protections
work page 2025
-
[4]
Anthropic. (2026). Claude Code documentation. https://code.claude.com/docs/en/overview
work page 2026
-
[5]
Anthropic. (2026). Responsible Scaling Policy Version 3.0. https://www.anthropic. com/news/responsible-scaling-policy-v3
work page 2026
- [6]
- [7]
-
[8]
Adversarial Poetry as a Universal Single-Turn Jailbreak Mechanism in Large Language Models,
P. Bisconti, M. Prandi, F. Pierucci, F. Giarrusso, M. Bracale, M. Galisai, V. Suriani, O. Sorokoletova, F. Sartore, and D. Nardi, “Adversarial Poetry as a Universal Single-Turn Jailbreak Mechanism in Large Language Models,”arXiv preprintarXiv:2511.15304, 2025. doi:10.48550/arXiv.2511.15304
-
[9]
Beyond Single- Agent Safety: A Taxonomy of Risks in LLM-to-LLM Interactions,
P. Bisconti, M. Galisai, F. Pierucci, M. Bracale, and M. Prandi, “Beyond Single- Agent Safety: A Taxonomy of Risks in LLM-to-LLM Interactions,”arXiv preprint arXiv:2512.02682, 2025. doi:10.48550/arXiv.2512.02682
-
[10]
From Adversarial Poetry to Adversarial Tales: An Interpretability Research Agenda,
P. Bisconti, M. Galisai, M. Prandi, F. Pierucci, O. Sorokoletova, F. Giarrusso, V. Suriani, M. Bracale, and D. Nardi, “From Adversarial Poetry to Adversarial Tales: An Interpretability Research Agenda,”arXiv preprintarXiv:2601.08837, 2026. doi:10.48550/arXiv.2601.08837
-
[11]
Bort, J. (2026). A Meta AI security researcher said an OpenClaw agent ran amok on her inbox.TechCrunch
work page 2026
-
[12]
(2020).The Brussels Effect: How the European Union Rules the World
Bradford, A. (2020).The Brussels Effect: How the European Union Rules the World. Oxford University Press
work page 2020
-
[13]
(2023).Digital Empires: The Global Battle to Regulate Technology
Bradford, A. (2023).Digital Empires: The Global Battle to Regulate Technology. Oxford University Press
work page 2023
-
[14]
Business Insider. (2025). Replit’s CEO apologizes after its AI agent wiped a company’s code base in a test run and lied about it. https://www.businessinsider.com/replit-ceo- apologizes-ai-coding-tool-delete-company-database-2025-7 39
work page 2025
-
[15]
CEN-CENELEC JTC 21. (2024). Standardisation request M/613 for AI
work page 2024
-
[16]
Chao, P., et al. (2024). JailbreakBench: An open robustness benchmark for jailbreaking large language models.arXiv:2404.01318
work page internal anchor Pith review Pith/arXiv arXiv 2024
- [17]
-
[18]
Available at: https://www.chinalawtranslate.com/en/22075-2/
China Law Translate.Cybersecurity Law of the People’s Republic of China (2026 revised version). Available at: https://www.chinalawtranslate.com/en/22075-2/. Last accessed: 19 May 2026
work page 2026
-
[19]
Available at: https://www.chinalawtranslate.com/en/ generative-ai-interim/
China Law Translate.Interim Measures for the Management of Generative Artifi- cial Intelligence Services. Available at: https://www.chinalawtranslate.com/en/ generative-ai-interim/. Last accessed: 19 May 2026
work page 2026
-
[20]
Coggins, S., Saeri, A., Daniell, K. A., Ruster, L. P., Liu, J., and Davis, J. L. (2025). The 2025 OpenAI Preparedness Framework does not guarantee any AI risk mitigation prac- tices: A proof-of-concept for affordance analyses of AI safety policies. arXiv:2509.24394. https://arxiv.org/abs/2509.24394
-
[21]
Costa, M., et al. (2025). Securing AI Agents with Information-Flow Control. arXiv:2505.23643
work page internal anchor Pith review Pith/arXiv arXiv 2025
-
[22]
Debenedetti, E., et al. (2025). Defeating Prompt Injections by Design.arXiv:2503.18813
work page internal anchor Pith review Pith/arXiv arXiv 2025
- [23]
- [24]
-
[25]
European Commission. (2022). The Blue Guide on the implementation of EU product rules
work page 2022
-
[26]
European Commission. (2025). Code of Practice for General-Purpose AI Models: Safety and Security Chapter
work page 2025
-
[27]
European Commission. (2025). Commission publishes list of signatories to the General- Purpose AI Code of Practice.https://www.politico.eu/article/eu-signatories-ai-code- practice-amazon-google-ibm-microsoft-ai/
work page 2025
-
[28]
European Commission. (2025). General-Purpose AI Code of Practice. https://digital- strategy.ec.europa.eu/en/policies/contents-code-gpai
work page 2025
-
[29]
European Parliament and Council of the European Union. (2024). Regulation (EU) 2024/1689 laying down harmonised rules on artificial intelligence
work page 2024
- [30]
-
[31]
Adversarial Humanities Benchmark: Results on Stylistic Robustness in Frontier Model Safety
M. Galisai, S. Cifani, F. Giarrusso, P. Bisconti, M. Prandi, F. Pierucci, F. Sartore, and D. Nardi, “Adversarial Humanities Benchmark: Results on Stylistic Robustness in Frontier Model Safety,”arXiv preprintarXiv:2604.18487, 2026. doi:10.48550/arXiv.2604.18487
work page internal anchor Pith review Pith/arXiv arXiv doi:10.48550/arxiv.2604.18487 2026
- [32]
-
[33]
Gehman, S., et al. (2020). RealToxicityPrompts: Evaluating neural toxic degeneration in language models. https://arxiv.org/abs/2009.11462Findings of EMNLP
work page internal anchor Pith review Pith/arXiv arXiv 2020
-
[34]
Available at: https://www.geopolitechs.org/p/china-issues-new-rules-on-ai-ethics
Geopolitechs.China Issues New Rules on AI Ethics Review and Support. Available at: https://www.geopolitechs.org/p/china-issues-new-rules-on-ai-ethics . Last accessed: 19 May 2026
work page 2026
-
[35]
Available at: https: //www.geopolitechs.org/p/chinas-first-policy-framework-for
Geopolitechs.China’s first policy framework for AI agents. Available at: https: //www.geopolitechs.org/p/chinas-first-policy-framework-for . Last accessed: 19 May 2026
work page 2026
- [36]
- [37]
-
[38]
Greshake, K., et al. (2023). Not what you’ve signed up for: Compromising Real-World LLM-Integrated Applications with Indirect Prompt Injection.arXiv:2302.12173
work page internal anchor Pith review Pith/arXiv arXiv 2023
-
[39]
The Guardian. (2026). Claude-powered AI agent’s confession after deleting a firm’s entire database. https://www.theguardian.com/technology/2026/apr/29/claude-ai-deletes-firm- database
work page 2026
- [40]
-
[41]
Hong, S., et al. (2023). MetaGPT: Meta Programming for A Multi-Agent Collaborative Framework.arXiv:2308.00352
work page internal anchor Pith review Pith/arXiv arXiv 2023
- [42]
-
[43]
Hubinger, E., et al. (2019). Risks from Learned Optimization in Advanced Machine Learning Systems.arXiv:1906.01820
work page internal anchor Pith review Pith/arXiv arXiv 2019
-
[44]
Hubinger, E., et al. (2024). Sleeper Agents: Training Deceptive LLMs that Persist Through Safety Training.arXiv:2401.05566
work page internal anchor Pith review Pith/arXiv arXiv 2024
-
[45]
Kaiyom, F. et al. (2024). HELM Safety: Towards standardized safety evaluations of language models
work page 2024
- [46]
-
[47]
Li, N., et al. (2024). The WMDP Benchmark: Measuring and reducing malicious use with unlearning.arXiv:2403.03218
work page internal anchor Pith review Pith/arXiv arXiv 2024
- [48]
-
[49]
Lin, S., Hilton, J., and Evans, O. (2022). TruthfulQA: Measuring how models mimic human falsehoods.ACL
work page 2022
-
[50]
Liu, X., et al. (2023). AgentBench: Evaluating LLMs as agents.arXiv:2308.03688
work page internal anchor Pith review Pith/arXiv arXiv 2023
-
[51]
Liu, Y., et al. (2023). Prompt Injection attack against LLM-integrated Applications. arXiv:2306.05499
work page internal anchor Pith review Pith/arXiv arXiv 2023
- [52]
-
[53]
Malik, S., et al. (2025). RewardBench 2: Advancing reward model evaluation. arXiv:2506.01937
work page internal anchor Pith review Pith/arXiv arXiv 2025
-
[54]
Mazeika, M., et al. (2024). HarmBench: A standardized evaluation framework for automated red teaming and robust refusal.ICML
work page 2024
-
[55]
Terminal-Bench: Benchmarking Agents on Hard, Realistic Tasks in Command Line Interfaces
Merrill, M. A., et al. (2026). Terminal-Bench: Benchmarking agents on hard, realistic tasks in command line interfaces.arXiv:2601.11868
work page internal anchor Pith review Pith/arXiv arXiv 2026
-
[56]
Nadeem, M., Bethke, A., and Reddy, S. (2021). StereoSet: Measuring stereotypical bias in pretrained language models.ACL
work page 2021
- [57]
-
[58]
Nangia, N., et al. (2020). CrowS-Pairs: A challenge dataset for measuring social biases in masked language models.EMNLP
work page 2020
-
[59]
Nannini, L., et al. (2026). AI agents under EU law.arXiv:2604.04604
work page internal anchor Pith review Pith/arXiv arXiv 2026
-
[60]
New York Post. (2026). Anthropic’s Claude Mythos model sparks fear of AI doomsday if released to public. https://nypost.com/2026/04/08/business/ anthropics-claude-mythos-model-sparks-fears-of-ai-doomsday-wave-of-devastating-hacks/
work page 2026
-
[61]
Nous Research. (2026). Hermes Agent documentation. https://hermes- agent.lzw.me/docs/en/
work page 2026
-
[62]
OpenAI. (2025). Preparedness Framework. https://openai.com/safety/ preparedness
work page 2025
-
[63]
OpenAI. (2026). Codex CLI features and approvals documentation. https://developers.openai.com/codex/cli/features
work page 2026
-
[64]
(2026).OpenClaw: Personal AI Assistant
OpenClaw maintainers. (2026).OpenClaw: Personal AI Assistant. GitHub repository. https://github.com/openclaw/openclaw 42
work page 2026
- [65]
-
[66]
Parrish, A., et al. (2022). BBQ: A hand-built bias benchmark for question answering. Findings of ACL
work page 2022
-
[67]
Bench-2-CoP: Can We Trust Benchmarking for EU AI Compliance? arXiv preprint arXiv:2508.05464, 2025
Matteo Prandi, Vincenzo Suriani, Federico Pierucci, Marcello Galisai, Daniele Nardi, and Piercosma Bisconti. Bench-2-CoP: Can We Trust Benchmarking for EU AI Compliance? arXiv preprint arXiv:2508.05464, 2025
- [68]
- [69]
-
[70]
Pierucci, F., Prandi, M., Bracale Syrnikov, M., Galisai, M., and Bisconti, P. (2026). Agentic microphysics: A manifesto for generative AI safety.arXiv:2604.15236
work page internal anchor Pith review Pith/arXiv arXiv 2026
-
[71]
Qin, Y., et al. (2023). ToolLLM: Facilitating Large Language Models to Master 16000+ Real-world APIs.arXiv:2307.16789
work page internal anchor Pith review Pith/arXiv arXiv 2023
- [72]
-
[73]
Available at: https://openstd.samr.gov
State Administration for Market Regulation and China National Standardization Admin- istration.GB/T 45654–2025 Cybersecurity Technology—Basic Security Requirements for Generative Artificial Intelligence Service. Available at: https://openstd.samr.gov. cn/bzgk/std/newGbInfo?hcno=F67D3F376E0A0A0FF5317FB36B32A30A. Last accessed: 19 May 2026
work page 2025
-
[74]
Available at: https://std.samr.gov.cn/gb/search/ gbDetailed?id=4C5277928DA2411EE06397BE0A0AE436
State Administration for Market Regulation.General Security Requirements for Artificial Intelligence Agent Application. Available at: https://std.samr.gov.cn/gb/search/ gbDetailed?id=4C5277928DA2411EE06397BE0A0AE436. Last accessed: 19 May 2026
work page 2026
-
[75]
Shinn, N., et al. (2023). Reflexion: Language Agents with Verbal Reinforcement Learning. arXiv:2303.11366
work page internal anchor Pith review Pith/arXiv arXiv 2023
- [76]
-
[77]
Souly, A., et al. (2024). A StrongREJECT for empty jailbreaks.arXiv:2402.10260
work page internal anchor Pith review Pith/arXiv arXiv 2024
- [78]
- [79]
-
[80]
P., Kaunismaa, J., and Panickssery, A
Sudhir, A. P., Kaunismaa, J., and Panickssery, A. (2025). A benchmark for scalable oversight protocols.arXiv:2504.03731. 43
discussion (0)
Sign in with ORCID, Apple, or X to comment. Anyone can read and Pith papers without signing in.