Jailbreak Attack Evaluation

Jailbreak attacks -- adversarial prompts that bypass LLM alignment through purely linguistic manipulation -- pose a growing operational security threat, yet the field lacks large-scale, reproducible infrastructure for generating, categorizing, and evaluating them systematically. This paper addresses that gap with three contributions. (1) Large-scale compositional jailbreak dataset. We construct 114,000 adversarial prompts by applying 912 composing strategies to 125 harmful seed prompts from JailBreakV-28K. Every prompt is assigned to one of 14 cybersecurity attack categories (e.g., malware, phishing, privilege escalation) via a six-model majority-vote pipeline, and each strategy is ranked by effectiveness per category, enabling principled strategy selection grounded in concrete adversarial objectives. (2) Automated jailbreak generation. We instruction-fine-tune category-aware LLMs on Moderate and Optimal subsets, producing models that synthesize fluent jailbreak prompts from a harmful seed at inference time -- no templates, no gradient search. Our generators achieve perplexity 24-39 versus 40-140 for AutoDAN and AmpleGCG, with safety-filter evasion rates of 0.29-0.51 Mal (LlamaPromptGuard-2-86M), enabling controllable, scalable red-teaming under realistic adversarial conditions. (3) OPTIMUS: a training-free jailbreak evaluator. OPTIMUS is a continuous metric J(S,H) that jointly captures semantic similarity between the harmful seed and the jailbreak (S) and harmfulness probability (H) via calibrated penalty functions. Unlike binary attack success rate (ASR), OPTIMUS requires no task-specific training, generalizes across evolving strategies, and exposes a stealth-optimal regime (S*=0.57, H*=0.43) that ASR misses. Experiments across 114,000 prompts confirm that OPTIMUS separates Weak, Moderate, and Optimal jailbreaks with category-level evidence binary evaluation cannot supply.

Many jailbreak attack research papers report attack success rates for a limited number of parameter settings, even though there are many combinations of parameter settings that could be used. Further, when new jailbreak papers are released, they often benchmark results against single configurations of existing attacks. This position paper argues such practices are fundamentally insufficient for characterising the threat posed by parameterised jailbreak attacks, and comparing attacks. Most jailbreak attacks expose multiple internal parameters, system prompt templates, conversation rounds, cipher dispersion, teaching shots, and ASR varies substantially across these parameters. Reporting only the best-case configuration discards two pieces of information that defenders genuinely need: how typical that performance is across the variant space, and how much of the attack surface is missed by selecting a single variant. We propose two new measures for jailbreak attacks: the Variant Sensitivity Measure (VSM) and Union Coverage (UC). VSM quantifies how far the best reported ASR deviates from the mean ASR across the tested variant space, UC is the total fraction of prompts resulting in unsafe responses across all tested configurations. We empirically demonstrate the importance of these measures using two attack families across three open-source target models. For PAIR, the best template reaches 69% ASR on Mistral-7B and 75% on Qwen3-0.6B, while UC rises to 88% and 93%, respectively. For bijection on Mistral-7B, the best variant reaches 81% ASR, but the 36-variant union covers 100% of HarmBench-100 prompts. We argue that distributional reporting, publishing VSM alongside ASR and enumerating variant coverage as fully as compute allows, should become the new minimum standard for parameterised jailbreak evaluation.

As language model safeguards become more robust, attackers are pushed toward developing increasingly complex jailbreaks. Prior work has found that this complexity imposes a "jailbreak tax" that degrades the target model's task performance. We show that this tax scales inversely with model capability and that the most advanced jailbreaks effectively yield no reduction in model capabilities. Evaluating 28 jailbreaks on five benchmarks across Claude models ranging in capability from Haiku 4.5 to Opus 4.6, we find Haiku 4.5 loses an average of 33.1% on benchmark performance when jailbroken, while Opus 4.6 at max thinking effort loses only 7.7%. We also observe that across all models, reasoning-heavy tasks display considerably more degradation than knowledge-recall tasks. Finally, Boundary Point Jailbreaking, currently the strongest jailbreak against deployed classifiers, achieves near-perfect classifier evasion with near-zero degradation across safeguarded models. We recommend that safety cases for frontier models should not rely on a meaningful capability degradation from jailbreaks.

Large language models remain vulnerable to jailbreak attacks, yet we still lack a systematic understanding of how jailbreak success scales with attacker effort across methods, model families, and harm types. We initiate a scaling-law framework for jailbreaks by treating each attack as a compute-bounded optimization procedure and measuring progress on a shared FLOPs axis. Our systematic evaluation spans four representative jailbreak paradigms, covering optimization-based attacks, self-refinement prompting, sampling-based selection, and genetic optimization, across multiple model families and scales on a diverse set of harmful goals. We investigate scaling laws that relate attacker budget to attack success score by fitting a simple saturating exponential function to FLOPs--success trajectories, and we derive comparable efficiency summaries from the fitted curves. Empirically, prompting-based paradigms tend to be the most compute-efficient compared to optimization-based methods. To explain this gap, we cast prompt-based updates into an optimization view and show via a same-state comparison that prompt-based attacks more effectively optimize in prompt space. We also show that attacks occupy distinct success--stealthiness operating points with prompting-based methods occupying the high-success, high-stealth region. Finally, we find that vulnerability is strongly goal-dependent: harms involving misinformation are typically easier to elicit than other non-misinformation harms.

Jailbreak techniques for large language models (LLMs) evolve faster than benchmarks, making robustness estimates stale and difficult to compare across papers due to drift in datasets, harnesses, and judging protocols. We introduce JAILBREAK FOUNDRY (JBF), a system that addresses this gap via a multi-agent workflow to translate jailbreak papers into executable modules for immediate evaluation within a unified harness. JBF features three core components: (i) JBF-LIB for shared contracts and reusable utilities; (ii) JBF-FORGE for the multi-agent paper-to-module translation; and (iii) JBF-EVAL for standardizing evaluations. Across 30 reproduced attacks, JBF achieves high fidelity with a mean (reproduced-reported) attack success rate (ASR) deviation of +0.26 percentage points. By leveraging shared infrastructure, JBF reduces attack-specific implementation code by more than half relative to original repositories and achieves an 82.5% mean reused-code ratio. This system enables a standardized AdvBench evaluation of all 30 attacks across 10 victim models using a consistent GPT-4o judge. By automating both attack integration and standardized evaluation, JBF offers a scalable solution for creating living benchmarks that keep pace with the rapidly shifting security landscape.

Despite the growing interest in jailbreaks as an effective red-teaming tool for building safe and responsible large language models (LLMs), flawed evaluation system designs have led to significant discrepancies in their effectiveness assessments. With a systematic measurement study based on 37 jailbreak studies since 2022, we find that existing evaluation systems lack case-specific criteria, resulting in misleading conclusions about their effectiveness and safety implications. In this paper, we introduce GuidedBench, a novel benchmark comprising a curated harmful question dataset and GuidedEval, an evaluation system integrated with detailed case-by-case evaluation guidelines. Experiments demonstrate that GuidedBench offers more accurate evaluations of jailbreak performance, enabling meaningful comparisons across methods. GuidedEval reduces inter-evaluator variance by at least 76.03%, ensuring reliable and reproducible evaluations. We reveal why existing jailbreak benchmarks fail to evaluate accurately and suggest better evaluation practices.