Rethinking LLM Jailbreak Evaluation: Continuous Risk Landscapes Beyond Binary Outcomes

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.

Large Language Models (LLMs) have achieved remarkable success but remain highly susceptible to jailbreak attacks, in which adversarial prompts coerce models into generating harmful, unethical, or policy-violating outputs. Such attacks pose real-world risks, eroding safety, trust, and regulatory compliance in high-stakes applications. Although a variety of attack and defense methods have been proposed, existing evaluation practices are inadequate, often relying on narrow metrics like attack success rate that fail to capture the multidimensional nature of LLM security. In this paper, we present a systematic taxonomy of jailbreak attacks and defenses and introduce Security Cube, a unified, multi-dimensional framework for comprehensive evaluation of these techniques. We provide detailed comparison tables of existing attacks and defenses, highlighting key insights and open challenges across the literature. Leveraging Security Cube, we conduct benchmark studies on 13 representative attacks and 5 defenses, establishing a clear view of the current landscape encompassing jailbreak attacks, defenses, automated judges, and LLM vulnerabilities. Based on these evaluations, we distill critical findings, identify unresolved problems, and outline promising research directions for enhancing LLM robustness against jailbreak attacks. Our analysis aims to pave the way towards more robust, interpretable, and trustworthy LLM systems. Our code is available at Code.

Large Language Models (LLMs) are trained to refuse harmful requests, yet they remain vulnerable to jailbreak attacks that exploit weaknesses in conversational safety mechanisms. We introduce Incremental Completion Decomposition ICD, a trajectory-based jailbreak strategy that elicits a sequence of single-word continuations related to a malicious request before eliciting the full response. In addition, we propose ICD variants that use model-generated or attacker-injected intermediate continuations, as well as final-response prefilling. We evaluate these variants across a broad set of open-weight model families, demonstrating superior Attack Success Rate (ASR) on AdvBench, JailbreakBench, and StrongREJECT compared to existing methods. In addition, we provide a theoretical account of why ICD is effective and present mechanistic evidence that successful attack trajectories suppress refusal-related representations and shift activations away from safety-aligned states.