Identically Trained Language Models Break on Different Jailbreaks

Safety fine-tuning of language models typically requires a curated adversarial dataset. We take a different approach: score each candidate prompt's difficulty by how often the target model's own rollouts are judged harmful, then fine-tune on the hardest prompts paired with the model's own non-jailbroken rollouts. On Llama-3-8B-Instruct and Llama-3.2-3B-Instruct, this approach cuts the WildJailbreak attack success rate from 11.5% and 20.1% down to 1-3%, but pushes refusal on jailbreak-shaped benign prompts from 14-22% to 74-94%. Interleaving the same hard prompts 1:1 with adversarially-framed benign prompts (prompts that look like jailbreaks but have benign intent) cuts that refusal back down to 30-51% on 8B and 52-72% on 3B, at a cost of 2-6 percentage points of attack success rate. Within the mixed regime, training on the hardest half of the eligible pool rather than a random half cuts the remaining ASR by 35-50% (about 3 percentage points) on both models.

Jailbreak methods are commonly compared using Attack Success Rate (ASR), but these comparisons depend on how responses are generated and judged. In this paper, we examine eight attacks against three open-weight language models using three evaluation procedures. Low-resource language attacks achieve a mean ASR of 96.0% under keyword matching but 2.7% under a Qwen3 evaluator following StrongREJECT scoring instructions. Changing the number and arrangement of attempts reverses the ranking of DeepInception and rewriting. In a separate experiment, sampling 100 responses for each unchanged request at Ollama's default temperature of 0.8 yields 100% ASR under keyword matching but 50% under the Qwen3 evaluator. Beyond evaluator sensitivity, these findings raise a safety concern: repeated sampling can expose residual unsafe behavior despite an initial refusal, suggesting probabilistic suppression rather than robust exclusion. We recommend explicit success definitions, matched response budgets, validated evaluators, and reporting cumulative failure under repeated interaction rather than relying on single-generation tests.

"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!