Safety-aligned language models are commonly deployed as multi-turn assistants, which lets adversaries spread unsafe intent across several user turns instead of a single prompt. Gradient-based jailbreak detectors such as GradSafe were developed for single prompts: they score an input by the alignment between its induced gradient and a fixed unsafe reference direction, and their effectiveness in multi-turn dialogue remains unclear. We conduct a controlled evaluation of gradient-based jailbreak detection in multi-turn settings. We extend GradSafe with a Context Window Scanner that applies the detector to fixed-size windows of user turns and uses the maximum window score as the conversation-level score. We evaluate different window sizes, attack families, benign conversation distributions, and target models. The results differ sharply between synthetic and realistic benign settings. Against synthetic benign conversations, the detector achieves an ROC-AUC of 0.98 on human-authored multi-turn jailbreaks. On WildChat benign conversations, ROC-AUC drops to 0.76, and a threshold calibrated on synthetic data flags more than 90% of benign conversations as unsafe. Under realistic benign distributions, single-turn windows give the highest separability, whereas longer windows and accumulated contexts reduce performance. The detector is also sensitive to the attack-generation method and target model: successful Crescendo attacks receive scores comparable to or lower than benign conversations, and Qwen2.5-7B-Instruct yields near-random separability with a different optimal window size. These findings show that gradient-based signals can support multi-turn jailbreak detection, but reliable deployment requires calibration on realistic benign conversations, short-window scoring, length-aware thresholds, and evaluation across attack types and model architectures.
Multi-turn jailbreak attacks progressively erode LLM safety alignment across seemingly innocuous conversation turns, achieving success rates exceeding 90% against state-of-the-art models. Existing alignment-based and guardrail methods suffer from three key limitations: they require costly weight modification, evaluate each turn independently without modeling cumulative safety erosion, and detect attacks only after harmful content has been generated. To address these limitations, we first formulate the proactive early jailbreak detection problem with a new metric, detection lead, that measures how early an attack can be detected before the LLM complies. We then propose SAFEDREAM, a lightweight world-model-based framework that operates as an external module without modifying the LLM's weights. SAFEDREAM introduces three components: (1) a safety state world model that encodes LLM hidden states into a compact safety representation and predicts how it evolves across turns, (2) CUSUM detection that accumulates weak per-turn risk signals into reliable evidence, and (3) contrastive imagination that simultaneously rolls out attack and benign futures in latent space to issue early alarms before jailbreaks occur. On three multi-turn jailbreak benchmarks (XGuard-Train, SafeDialBench, SafeMTData) against 8 baselines, SAFEDREAM achieves the best detection timeliness across all benchmarks (1.06-1.20 turns before compliance) while maintaining competitive false positive rates and outperforming baselines in detection quality.
Bo Yan, Weikai Lin, Yada Zhu +1
University of Central Florida · University of Rochester · IBM Research
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 jailbreaks can evade turn-level moderation by spreading unsafe intent across a dialogue through gradual escalation, reframing, and role manipulation. We address multi-turn jailbreak detection as a conversation-level classification problem and introduce an efficient hierarchical detector that avoids expensive long-context concatenation while retaining cross-turn reasoning. The model encodes individual turns to form compact turn representations and applies a lightweight conversation module that captures dialogue dynamics and selectively attends to fine-grained evidence when needed. On a challenging evaluation benchmark of 14,038 conversations, our approach achieves an F1 of 0.9394, outperforming Claude Opus 4.7, the strongest competing baseline, by 0.07 while halving its false-positive rate. Ablation studies confirm that each architectural component contributes meaningfully, with combining cross-attention and self-attention in the conversation module yielding a 2.26 percentage point reduction in false-positive rate over the self-attention-only variant.