mlsanityData to 7 Oct 2026

The Great Pretender: A Stochasticity Problem in LLM Jailbreak

arXiv 2605.14418 ↗First posted 14 May 2026cs.CR cs.AIcited by 1

On the map: LLM safety and security → Jailbreaking

Abstract (arXiv)

"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!

Key facts. Cited by 1 paper in the map (data through 7 Oct 2026). Placed in Jailbreaking, one of 12 directions in LLM safety and security. Builds on 8 of its 14 references that are in the map. First posted on arXiv 14 May 2026.

Builds on

8 of 14 references.

Closest ancestors · 5

Same direction, newest first

  1. 2026Statistical Estimation of Adversarial Risk in Large Language Models under Best-of-N Sampling30 Jan
  2. 2024Great, Now Write an Article About That: The Crescendo Multi-Turn LLM Jailbreak Attack2 Apr
  3. 2024JailbreakBench: An Open Robustness Benchmark for Jailbreaking Large Language Models28 Mar
  4. 2023Tree of Attacks: Jailbreaking Black-Box LLMs Automatically4 Dec
  5. 2023Jailbreaking Black Box Large Language Models in Twenty Queries12 Oct

Other references · 3

  1. 2023Llama Guard: LLM-based Input-Output Safeguard for Human-AI Conversationscited by 1,124
  2. 2025Fine-Tuning Lowers Safety and Disrupts Evaluation Consistencycited by 25
  3. 2026A Coin Flip for Safety: LLM Judges Fail to Reliably Measure Adversarial Robustnesscited by 20

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Cited by year (2026 to 7 Oct)

Citing papers per year: 2026: 1.

1 paper.