D-Judge: Disrupting Multi-Turn Jailbreaks using Semantics-Preserving Output Rewriting

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.

Multi-turn jailbreak attacks pose a growing threat to LLMs by exploiting conversational dynamics such as gradual escalation and cross-turn coordination. Existing defenses either rely on costly retraining -- often degrading model utility -- or apply single-turn analysis independently at each turn, failing to capture how risk accumulates along interaction trajectories. We observe that safety behavior in multi-turn interaction is trajectory-dependent: dialogue history continuously reshapes the model's conditioning context, making it insufficient to evaluate each turn in isolation. Motivated by this insight, we present THRD, the first training-free framework that explicitly models temporal risk accumulation for multi-turn jailbreak defense. THRD integrates four modules: a Turn-level Risk Assessor (TRA) for instantaneous risk estimation, a Historical Context Analyzer (HCA) for cross-turn intent escalation detection, a Response Evaluator (RE) for identifying facilitative outputs, and a Decision Module that combines these signals through a time-evolving scoring mechanism with attenuation-based modulation and trend-aware adjustment. Experiments against state-of-the-art multi-turn attacks -- including tree-search-based and multi-agent collaborative methods -- across two target models show that THRD reduces ASR to 0.2--4.0% while preserving model utility within 1.5% degradation on MMLU and GSM8K. Ablation studies confirm non-redundant module contributions and stable cross-architecture generalization. Analysis of first rejection triggers reveals that over 70% of multi-turn attacks require Turn~2 or later to detect, validating the necessity of explicit temporal aggregation.

Multi-turn jailbreaks exploit the ability of large language models to accumulate and act on conversational context. Instead of stating a harmful request directly, an attacker can gradually steer the conversation toward an unsafe answer. Recent methods demonstrate this risk, but they are usually evaluated as black-box pipelines with different budgets, judges, retry rules, and strategy generation procedures. As a result, it is often unclear whether reported gains reflect stronger attack mechanisms or different experimental conditions. We introduce MT-JailBench, a modular evaluation framework for benchmarking multi-turn jailbreaks under fixed conditions. MT-JailBench implements each attack as five interacting modules: evaluation function, attack strategy, prompt generation, prompt refinement, and flow control. This design enables fair comparison across attack methods and component-wise analysis of what drives attack success. Using MT-JailBench, we find that resource budgets and evaluation functions are major confounders: controlling turns, retries, interactions, sampled strategies, and judges substantially change the ranking of attacks. At the component level, prompt generation accounts for most performance variation, while refinement and flow control provide moderate gains. We also find that explicit dynamic strategy generation is not always necessary; stochastic sampling from a fixed strategy can rival more elaborate diversification mechanisms. Finally, recomposing the best components yields a strong attack configuration that outperforms its source attacks and generalizes across diverse target LLMs. MT-JailBench therefore provides a modular framework for comparing multi-turn jailbreaks, understanding the impact of components, and guiding stronger red-teaming evaluations.