HarDBench: A Benchmark for Draft-Based Co-Authoring Jailbreak Attacks for Safe Human-LLM Collaborative Writing

We present MultiBreak, a scalable and diverse multi-turn jailbreak benchmark to evaluate large language model (LLM) safety. Multi-turn jailbreaks mimic natural conversational settings, making them easier to bypass safety-aligned LLM than single-turn jailbreaks. Existing multi-turn benchmarks are limited in size or rely heavily on templates, which restrict their diversity. To address this gap, we unify a wide range of harmful jailbreak intents, and introduce an active learning pipeline for expanding high-quality multi-turn adversarial prompts, where a generator is iteratively fine-tuned to produce stronger attack candidates, guided by uncertainty-based refinement. Our MultiBreak includes 10,389 multi-turn adversarial prompts, spans 2,665 distinct harmful intents, and covers the most diverse set of topics to date. Empirical evaluation shows that our benchmark achieves up to a 54.0 and 34.6 higher attack success rate (ASR)} than the second-best dataset on DeepSeek-R1-7B and GPT-4.1-mini, respectively. More importantly, safety evaluations suggest that diverse attack categories uncover fine-grained LLM vulnerabilities}, and categories that appear benign under single-turn can exhibit substantially higher adversarial effectiveness in multi-turn scenarios. These findings highlight persistent vulnerabilities of LLMs under realistic adversarial settings and establish MultiBreak as a scalable resource for advancing LLM safety.

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 remain a critical threat to the safe deployment of large language models (LLMs). While prior work has primarily studied attacks and defenses at the prompt level, we show that this prompt-centric paradigm overlooks a structural vulnerability in stateful, function-calling environments. In such applications, developer-defined schemas, structured arguments, and untrusted tool outputs are interleaved into a single shared model context. This architecture expands the attack surface by blurring the boundary between trusted control logic and untrusted data, allowing adversarial intent to be distributed across a multi-turn execution path. We exploit this architectural flaw through SMT, a black-box attack framework based on Simulated Moderation Traces. Departing from purely prompt-based interactions, SMT constructs a multi-turn trajectory that simulates a legitimate moderation-auditing workflow. Within this trajectory, a fabricated moderation frame leverages red-team testing as a pretext to elicit harmful generations. The subsequent validation feedback treats safety refusals as execution failures, prompting refinements that gradually weaken the model's safety constraints and ultimately trigger harmful outputs. Extensive empirical evaluations on prominent commercial LLMs from five different providers across two standardized safety benchmarks show that SMT consistently achieves the highest average attack success rate and HarmScore while requiring a near-minimal number of queries, substantially outperforming existing baselines. These findings demonstrate that prompt-level sanitization alone is fundamentally insufficient for defending tool-enabled LLM systems and highlight the urgent need for context-aware validation across schemas, arguments, tool outputs, and accumulated conversation state. The code is available at https://github.com/liujlong27/SMT.