Adaptive Prompt Embedding Optimization for LLM Jailbreaking

Jailbreak attacks expose persistent safety weaknesses in large language models (LLMs), but existing stateless single-turn methods face a trade-off: hand-crafted prompts are expressive but static, while iterative prompt optimization can adapt but often relies on low-level mutations that require many target queries. We propose JailbreakOPT, a tool-assisted framework for improving iterative single-turn jailbreak prompt optimization. JailbreakOPT organizes diverse atomic jailbreak prompts into an attack tool library and composes them through a unified intra-episode optimization abstraction to generate stronger standalone attack prompts. To reuse experience across attack episodes, JailbreakOPT further frames tool selection as a contextual bandit problem and applies contextual Thompson sampling to guide exploration and exploitation based on past outcomes. Experiments across multiple target LLMs and attack goals show that JailbreakOPT improves attack success rate (ASR) while reducing the number of attacks until success (No.A) compared with atomic single-turn attacks and existing iterative optimization baselines. This paper may contain offensive or harmful content.

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.

Jailbreak attacks expose a persistent gap between the intended safety behavior of aligned large language models and their behavior under adversarial prompting. Existing automated methods are increasingly effective but each commits to a single attack family (e.g., one refinement loop, one tree search, one mutation space, or one strategy library) and no single family dominates: the best-performing method shifts across target models and harm categories, suggesting complementary strengths that per-prompt composition could exploit. We introduce LASH (LLM Adaptive Semantic Hybridization), a black-box framework that treats outputs from multiple base attacks as reusable seed prompts and adaptively composes them for each target request. Given a seed pool, LASH searches over seed subsets and softmax-normalized mixture weights; a composition module synthesizes a single candidate prompt, and a derivative-free genetic optimizer updates the weights using black-box target feedback and a two-stage fitness function combining keyword-based refusal detection with LLM-judge scoring. On JailbreakBench, which contains 100 harmful prompts across 10 categories, we evaluate LASH on six common target models. LASH achieves an average attack success rate of 84.5% under keyword-based evaluation and 74.5% under two-stage evaluation, where responses are first filtered for refusals and then scored by an LLM judge for whether they substantively fulfill the original harmful request. LASH outperforms five state-of-the-art baselines on both metrics with only 30 mean target queries. LASH also remains competitive under three defense mechanisms and induces more success-like internal representations. These results suggest that adaptive composition across heterogeneous jailbreak strategies is a promising direction for black-box red-teaming.