The Great Pretender: A Stochasticity Problem in LLM Jailbreak

Computer Science > Cryptography and Security [Submitted on 14 May 2026] The Great Pretender: A Stochasticity Problem in LLM Jailbreak Jean-Philippe Monteuuis, Cong Chen, Jonathan Petit "Oh-Oh, yes, I'm the great pretender. Pretending that I'm doing well. My need is such, I pretend too much..." summarizes the state in the area of jailbreak creation and evaluation. You find this method to generate adversarial attacks proposed by a reputable institution (e.g., BoN from Anthropic or Crescendo from Microsoft Research). However, this method does not deliver on the promise claimed in the paper despite having top ASR scores against industry-grade LLMs. You successfully generate the jailbreak prompts against your target (open) model. However, the generated jailbreak prompt works against the target model with a 50% consecutive success rate (5 out of 10 attempts) despite having an 80% ASR (on paper) on the latest closed-source model (with a guardrail system)! This observation leads us to think. First, Attack Success Rate (ASR), the primary metric for LLM jailbreak benchmarking, is not a stable quantity. Second, published ASR numbers are therefore systematically inflated and incomparable across papers. Therefore, we wonder "Why a successful jailbreak prompt does not perform consistently well against a target model on which the prompts have been optimized?". To answer this question, we study the impact of stochasticity not only during attack evaluation but also during attack generation. Our evaluation includes several jailbreak attacks, models (different sizes and providers), and judges. In addition, we propose a new metric and two new frameworks (CAS-eval and CAS-gen). Our evaluation framework, CAS-eval, shows that an attack can have an ASR drop of up to 30 percentage points when a jailbreak prompt needs to succeed on more than one attempt. Thankfully, our attack generation framework (CAS-gen) improves previous jailbreak methods and helps them recover this loss of 30 percentage points! Subjects: Cryptography and Security (cs.CR); Artificial Intelligence (cs.AI) Cite as: arXiv:2605.14418 [cs.CR]   (or arXiv:2605.14418v1 [cs.CR] for this version)   https://doi.org/10.48550/arXiv.2605.14418 Focus to learn more Submission history From: Jean-Philippe Monteuuis [view email] [v1] Thu, 14 May 2026 06:05:37 UTC (938 KB) Access Paper: HTML (experimental) view license Current browse context: cs.CR < prev   |   next > new | recent | 2026-05 Change to browse by: cs cs.AI References & Citations NASA ADS Google Scholar Semantic Scholar Export BibTeX Citation Bookmark Bibliographic Tools Bibliographic and Citation Tools Bibliographic Explorer Toggle Bibliographic Explorer (What is the Explorer?) Connected Papers Toggle Connected Papers (What is Connected Papers?) Litmaps Toggle Litmaps (What is Litmaps?) scite.ai Toggle scite Smart Citations (What are Smart Citations?) Code, Data, Media Demos Related Papers About arXivLabs Which authors of this paper are endorsers? | Disable MathJax (What is MathJax?)