SoK: Systematizing LLM Prompt Security: Taxonomies, Datasets, and Unified Evaluation of Attacks and Defenses

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.

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.

Published evaluations of prompt-injection and jailbreak detectors for Large Language Models often suffer from two systematic weaknesses: per-dataset threshold tuning and undisclosed operating points. We describe an evaluation harness that addresses both. The detector under evaluation is scored across 16 public benchmarks (12,111 samples) using 5-fold cross-validation. StratifiedKFold (by row) is the headline pass; a parallel StratifiedGroupKFold pass over a composite key (parent-prompt id plus MinHash + LSH near-duplicate clusters at Jaccard $\gtrsim 0.8$) runs alongside it as a leakage-premium diagnostic. A single global operating point is selected on the held-out folds (max F1 subject to FPR $\leq 1\%$) and applied uniformly to every dataset, so per-dataset results reflect one threshold rather than per-benchmark optimisation. Generalisation is examined through a battery of diagnostics (leave-one-dataset-out cross-validation, a random-label control, adversarial validation, permutation feature importance, length-bias correlation, classifier-head agreement, cross-source near-duplicate detection, threshold transferability, train-vs-OOF agreement, and a paraphrase-invariance probe), most with a quantitative pass threshold and the remainder with a stated failure mode. For every external comparison, the detector's threshold is re-tuned to the competitor's published false-positive rate so head-to-head values are evaluated at matched operating points.