TAO-Attack: Toward Advanced Optimization-Based Jailbreak Attacks for Large Language Models

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.

Despite the significant efforts devoted to aligning large language models (LLMs) with human values and ensuring safe deployment, recent work has revealed that LLMs remain vulnerable to adversarial jailbreak attacks that can bypass safety guardrails and elicit harmful responses. Many defense methods are proposed to detect jailbreaks but they are limited in their effectiveness to counter wide-range optimization-based jailbreak mechanisms that can yield highly fluency-optimized or harmful semantic obfuscated prompts. To tackle this challenge, we propose a unified detection framework SAFEGuard which incorporates a hybrid fluency measurement based on cross-layer distribution distance and perplexity, and the analysis of harmful semantics through gradient matching. Our method is grounded in a paramount observation: high fluency prompts maintain their malicious intention close to harmful prompts while harmful semantic obfuscated prompts often inject gibberish token sequences. Our evaluation demonstrates that SAFEGuard consistently outperforms state-of-the-art baselines and achieves significant improvement in accuracy across different optimization-based jailbreaks. This underscores the effectiveness of SAFEGuard against evolving jailbreak attacks.

Despite rigorous safety alignment, Large Language Models (LLMs) remain vulnerable to jailbreak attacks. Existing black-box methods often rely on heuristic templates or exhaustive trials, lacking mechanistic interpretability and query efficiency. In this study, we investigate an intrinsic vulnerability in the safety mechanisms of LLMs, where safety alignment relies on a small set of sparsely distributed attention heads, leaving much of the representational space weakly monitored. We formalize this phenomenon with a mathematical jailbreaking model that characterizes the delicate boundary of effective text obfuscation and analytically explains observed jailbreak behaviors. Guided by this model, we propose Babel, an efficient black-box attack framework that exploits the identified safety gap through systematic obfuscation sampling with iterative, feedback-driven distribution refinement, enabling reliable and high-success jailbreak attacks without access to model internals. Comprehensive evaluations on frontier commercial models demonstrate that Babel achieves state-of-the-art attack success rates and superior query efficiency. Specifically, compared to state-of-the-art methods, Babel increases the attack success rate on GPT-4o from 41.33% to 82.67% and on Claude-3-5-haiku from 38.33% to 78.33% within an average of 40 queries, providing a robust red-teaming methodology for LLMs safety research.