# The Great Pretender: A Stochasticity Problem in LLM Jailbreak

arXiv: https://arxiv.org/abs/2605.14418 · HTML: https://mlsanity.com/paper/2605.14418/

## Key facts

- Cited by 3 papers in the map (data through 14 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.

## Placed in

- LLM safety and security / [Jailbreaking](https://mlsanity.com/safety/jailbreaking/)

## Builds on (most cited first, 8 of 8)

- [Jailbreaking Black Box Large Language Models in Twenty Queries](https://mlsanity.com/paper/2310.08419/) (2023)
- [Llama Guard: LLM-based Input-Output Safeguard for Human-AI Conversations](https://mlsanity.com/paper/2312.06674/) (2023)
- [Tree of Attacks: Jailbreaking Black-Box LLMs Automatically](https://mlsanity.com/paper/2312.02119/) (2023)
- [JailbreakBench: An Open Robustness Benchmark for Jailbreaking Large Language Models](https://mlsanity.com/paper/2404.01318/) (2024)
- [Great, Now Write an Article About That: The Crescendo Multi-Turn LLM Jailbreak Attack](https://mlsanity.com/paper/2404.01833/) (2024)
- [Fine-Tuning Lowers Safety and Disrupts Evaluation Consistency](https://mlsanity.com/paper/2506.17209/) (2025)
- [A Coin Flip for Safety: LLM Judges Fail to Reliably Measure Adversarial Robustness](https://mlsanity.com/paper/2603.06594/) (2026)
- [Statistical Estimation of Adversarial Risk in Large Language Models under Best-of-N Sampling](https://mlsanity.com/paper/2601.22636/) (2026)

## Built on by (most cited first, 3 of 3)

- [Depth, Not Breadth: Best-of-N Jailbreaking Beyond Surface Noise](https://mlsanity.com/paper/2607.26639/) (2026)
- [Clean Engineering, Unstable Measurement: A Preregistered Reliability Failure of Black-Box LLM Observers on Shared Endpoints](https://mlsanity.com/paper/2609.04198/) (2026)
- [MLCommons Jailbreak Benchmark v1.0](https://mlsanity.com/paper/2610.02827/) (2026)

## 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!