How Reliable Is Your Jailbreak Judge? Calibration and Adversarial Robustness of Automated ASR Scoring

"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!

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.

Automatic safety judges -- systems such as Llama Guard or a GPT-4o grading prompt that decide whether a model's reply is harmful -- produce the numbers behind almost every reported jailbreak success rate, defense evaluation, and safety leaderboard. We ask whether these judges grade what a reply contains or how it sounds. We keep a reply's content fixed and add content-invariant style wrappers: fixed strings placed before or after the reply that change only its tone (an educational disclaimer, a fake safety "reasoning" block, a token refusal followed by the unchanged harmful body), or, on harmless refusals, framing that merely sounds dangerous. The body is preserved byte-for-byte, so a faithful judge must return the same verdict, and any flip is an error of the judge, not a change in safety. Over 600 JailbreakBench replies x up to 7 forms x 8 judges, we measure flip rates with paired significance tests and measured noise floors. Findings are precise rather than universal: most judges barely move, but specific judges harbor cheaply exploitable blind spots. A token-refusal wrapper flips 19.9% of GPT-4o-mini's correct "unsafe" verdicts (noise floor 0.5%; 18.2% under majority-of-three re-scoring) yet moves Claude only 0.4%. The deployed Llama Guard 4 is deterministically gamed: an "educational course" framing flips 12.3% of its harmful verdicts to safe. A second deployed guard (gpt-oss-safeguard-20b) is immune, and rewriting only the grading prompt (StrongREJECT-style) cuts the attack tenfold on the identical model -- the vulnerability lives in the judge, not the content. A two-annotator human validation confirms 100% content invariance and 90% of flips as judge errors (kappa 0.95-1.0), and a bootstrap shows the underlying model ranking is already unstable to sampling alone. We release the dataset, wrappers, code, and per-verdict labels.