# Rethinking How to Evaluate Language Model Jailbreak

arXiv: https://arxiv.org/abs/2404.06407 · HTML: https://mlsanity.com/paper/2404.06407/

## Key facts

- Cited by 12 papers in the map (data through 14 Oct 2026).
- Placed in Reasoning for agents, planning and code, one of 17 directions in LLM reasoning.
- Builds on 0 of its 51 references that are in the map.
- First posted on arXiv 9 Apr 2024.

## Placed in

- LLM reasoning / [Reasoning for agents, planning and code](https://mlsanity.com/lr/reasoning-for-agents-planning-and-code/)
- LLM safety and security / [Jailbreaking](https://mlsanity.com/safety/jailbreaking/)

## Built on by (most cited first, 12 of 12)

- [Don't Say No: Jailbreaking LLM by Suppressing Refusal](https://mlsanity.com/paper/2404.16369/) (2024)
- [JAILJUDGE: A Comprehensive Jailbreak Judge Benchmark with Multi-Agent Enhanced Explanation Evaluation Framework](https://mlsanity.com/paper/2410.12855/) (2024)
- [SHIELD: Evaluation and Defense Strategies for Copyright Compliance in LLM Text Generation](https://mlsanity.com/paper/2406.12975/) (2024)
- [The Scales of Justitia: A Comprehensive Survey on Safety Evaluation of LLMs](https://mlsanity.com/paper/2506.11094/) (2025)
- [AutoJailbreak: Exploring Jailbreak Attacks and Defenses through a Dependency Lens](https://mlsanity.com/paper/2406.03805/) (2024)
- [Unlearning That Lasts: Utility-Preserving, Robust, and Almost Irreversible Forgetting in LLMs](https://mlsanity.com/paper/2509.02820/) (2025)
- [Toward Safer Diffusion Language Models: Discovery and Mitigation of Priming Vulnerability](https://mlsanity.com/paper/2510.00565/) (2025)
- [From ASR to ASP: Evaluating Prompt Attack Vulnerabilities Against Open-Source LLMs](https://mlsanity.com/paper/2505.14368/) (2025)
- [Beyond Jailbreaks: Revealing Stealthier and Broader LLM Security Risks Stemming from Alignment Failures](https://mlsanity.com/paper/2506.07402/) (2025)
- [LLM in the Middle: A Systematic Review of Threats and Mitigations to Real-World LLM-based Systems](https://mlsanity.com/paper/2509.10682/) (2025)
- [When Scanners Lie: Evaluator Instability in LLM Red-Teaming](https://mlsanity.com/paper/2603.14633/) (2026)
- [Knowledge-to-Jailbreak: Investigating Knowledge-driven Jailbreaking Attacks for Large Language Models](https://mlsanity.com/paper/2406.11682/) (2024)

## Abstract (arXiv)

Large language models (LLMs) have become increasingly integrated with various applications. To ensure that LLMs do not generate unsafe responses, they are aligned with safeguards that specify what content is restricted. However, such alignment can be bypassed to produce prohibited content using a technique commonly referred to as jailbreak. Different systems have been proposed to perform the jailbreak automatically. These systems rely on evaluation methods to determine whether a jailbreak attempt is successful. However, our analysis reveals that current jailbreak evaluation methods have two limitations. (1) Their objectives lack clarity and do not align with the goal of identifying unsafe responses. (2) They oversimplify the jailbreak result as a binary outcome, successful or not. In this paper, we propose three metrics, safeguard violation, informativeness, and relative truthfulness, to evaluate language model jailbreak. Additionally, we demonstrate how these metrics correlate with the goal of different malicious actors. To compute these metrics, we introduce a multifaceted approach that extends the natural language generation evaluation method after preprocessing the response. We evaluate our metrics on a benchmark dataset produced from three malicious intent datasets and three jailbreak systems. The benchmark dataset is labeled by three annotators. We compare our multifaceted approach with three existing jailbreak evaluation methods. Experiments demonstrate that our multifaceted evaluation outperforms existing methods, with F1 scores improving on average by 17% compared to existing baselines. Our findings motivate the need to move away from the binary view of the jailbreak problem and incorporate a more comprehensive evaluation to ensure the safety of the language model.