JailbreakOPT: Tool-Assisted Iterative Jailbreak Prompt Optimization

With a profusion of jailbreaks for LLMs now widely known, a growing concern is that non-expert malicious actors ("the average Jane") could elicit actionable responses to malicious requests. In this work, we examine whether this concern is justified. A non-expert malicious actor requires two ingredients for a successful attack: a powerful jailbreak for their target model, acting on an effective malicious query. For the former, we propose a novel attack strategy based on the multi-armed bandit framework. This allows efficient online learning of the optimal jailbreak from a large choice set via noisy exploration on a small number of queries, with subsequent application of the learnt policy on an exploitation set. For the latter, we curate $\mathrm{FrankensteinBench}$, a safety benchmark of $11,279$ malicious queries drawn from manual curation over $7$ existing benchmarks, along with automated enhancement and generation. Each query is categorized as simple or complex by the technical expertise required to craft it. Our findings confirm the concern. Our bandit-based attack achieves success rates as high as $97\%$ on average over $15$ SoTA open-weight LLMs. Moreover, adding complexity to queries raises the attack success rate by up to $26\%$ on average across models -- making it an effective, automatable prompting strategy.

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.

Existing white-box jailbreak attacks against aligned LLMs typically append discrete adversarial suffixes to the user prompt, which visibly alters the prompt and operates in a combinatorial token space. Prior work has avoided directly optimizing the embeddings of the original prompt tokens, presumably because perturbing them risks destroying the prompt's semantic content. We propose Prompt Embedding Optimization (PEO), a multi-round white-box jailbreak that directly optimizes the embeddings of the original prompt tokens without appending any adversarial tokens, and show that the concern is unfounded: the optimized embeddings remain close enough to their originals that the visible prompt string is preserved exactly after nearest-token projection, and quantitative analysis shows the model's responses stay on topic for the large majority of prompts. PEO combines continuous embedding-space optimization with structured continuation targets and an adaptive failure-focused schedule. Counterintuitively, later PEO rounds can benefit from heuristic composite response scaffolds that are not natural standalone templates, yet ASR-Judge shows that the resulting gains are not merely empty formatting or scaffold-only outputs. Across two standard harmful-behavior benchmarks and competing white-box attacks spanning discrete suffix search, appended adversarial embeddings, and search-based adversarial generation, PEO outperforms all of them in our experiments.