Semi-Automated Detection of Gaps in LLM Security Knowledge

Large Language Models (LLMs) are increasingly used as interfaces to information, code, and real-world services, making prompt-level security failures a practical concern. Although jailbreak attacks, defenses, datasets, and automated judgers have advanced rapidly, evaluation remains fragmented across threat models, access assumptions, cost budgets, datasets, and success criteria. This makes reported attack success rates and defense gains hard to compare. This SoK systematizes LLM prompt security across concepts, data, tooling, and measurement. We propose linked taxonomies for jailbreak attacks, defenses, and model vulnerabilities, while separating technical mechanisms from attacker and defender capabilities. We also formalize threat, access, and cost assumptions as explicit evaluation metadata. To support reproducible evaluation, we release JailbreakDB, PromptSecurity-Eval, and PromptSecurity, a modular platform that represents each experiment as a tuple of model, attack, defense, dataset, and judger. Using matched evaluations across models, attacks, defenses, and judgers, we show that access regime, native harmful-query behavior, attack cost, defense backfire, taxonomy subcategory, and judger choice all materially affect security conclusions. Together, these artifacts support reproducible, cost-aware, and taxonomy-grounded evaluation of LLM prompt security. Leaderboard: https://datasec-lab.github.io/PromptSecurityLeaderboard/. Dataset: https://huggingface.co/datasets/youbin2014/JailbreakDB. GitHub: https://github.com/datasec-lab/PromptSecurity.

Large language models (LLMs) now support automated software security tasks, including vulnerability discovery and proof-of-concept (PoC) generation. Existing benchmarks do not faithfully evaluate LLMs in real-world bug hunting scenarios because they rely on fuzzing harnesses, target-specific descriptions, or vulnerability-reproduction tasks. We present SEC-bench Pro, a benchmark for measuring agent bug hunting on critical, high-complexity software systems. This work discloses reports with concrete PoC inputs and links fixes into reproducible tasks through a three-phase pipeline for vulnerability collection, environment reconstruction, and oracle-based validation. We instantiate SEC-bench Pro with 183 validated vulnerabilities across V8 and SpiderMonkey, including a V8 subset with more than $1.5 million in cumulative Google Vulnerability Reward Program awards. These instances span memory-safety, sandbox, JIT, and race-condition bugs under browser-grade and runtime-grade execution conditions. Our evaluation shows that coding agents with frontier models remain below 40% success on both evaluated engines. The open-weight Kimi-K2.6 baseline reaches 11.7% on V8, while the strongest frontier configuration reaches 32.0% on V8 and 38.8% on SpiderMonkey. ClaudeCode and Codex solve complementary instance sets, and their two-agent union reaches 37.9% on V8 and 48.8% on SpiderMonkey. SEC-bench Pro provides robust environments for assessing LLM-based security agents and exposes limitations in long-horizon bug hunting tasks.

Large Language Models (LLMs) are widely used for code generation, yet their security behavior in realistic development workflows remains underexplored. Existing benchmarks often rely on explicitly specified security requirements, failing to capture real-world scenarios where prompts are frequently ambiguous or incomplete. In this paper, we adopt a developer-centric perspective and identify three representative risk scenarios that commonly lead to security vulnerabilities in LLM-generated code: Ambiguous Requirements, Under-Specified Operational Context, and Security--Functionality Conflict. Based on these scenarios, we construct a large-scale benchmark comprising 2,700 test cases, enabling fine-grained evaluation of LLM security under realistic conditions. Extensive evaluation of eight state-of-the-art LLMs reveals that all models exhibit average vulnerability rates exceeding 56% across risk scenarios. We further demonstrate that security-aware prompting can substantially mitigate these risks, achieving up to 45% improvement.