Mingqian Feng

Multi-turn jailbreaks capture the real threat model for safety-aligned chatbots, where single-turn attacks are merely a special case. Yet existing approaches break under exploration complexity and intent drift. We propose SEMA, a simple yet effective framework that trains a multi-turn attacker without relying on any existing strategies or external data. SEMA comprises two stages. Prefilling self-tuning enables usable rollouts by fine-tuning on non-refusal, well-structured, multi-turn adversarial prompts that are self-generated with a minimal prefix, thereby stabilizing subsequent learning. Reinforcement learning with intent-drift-aware reward trains the attacker to elicit valid multi-turn adversarial prompts while maintaining the same harmful objective. We anchor harmful intent in multi-turn jailbreaks via an intent-drift-aware reward that combines intent alignment, compliance risk, and level of detail. Our open-loop attack regime avoids dependence on victim feedback, unifies single- and multi-turn settings, and reduces exploration complexity. Across multiple datasets, victim models, and jailbreak judges, our method achieves state-of-the-art (SOTA) attack success rates (ASR), outperforming all single-turn baselines, manually scripted and template-driven multi-turn baselines, as well as our SFT (Supervised Fine-Tuning) and DPO (Direct Preference Optimization) variants. For instance, SEMA performs an average $80.1\%$ ASR@1 across three closed-source and open-source victim models on AdvBench, 33.9% over SOTA. The approach is compact, reproducible, and transfers across targets, providing a stronger and more realistic stress test for large language model (LLM) safety and enabling automatic redteaming to expose and localize failure modes. Our code is available at: https://github.com/fmmarkmq/SEMA.

Large Language Models (LLMs) are typically evaluated for safety under single-shot or low-budget adversarial prompting, which underestimates real-world risk. In practice, attackers can exploit large-scale parallel sampling to repeatedly probe a model until a harmful response is produced. While recent work shows that attack success increases with repeated sampling, principled methods for predicting large-scale adversarial risk remain limited. We propose a scaling-aware Best-of-N estimation of risk, SABER, for modeling jailbreak vulnerability under Best-of-N sampling. We model sample-level success probabilities using a Beta distribution, the conjugate prior of the Bernoulli distribution, and derive an analytic scaling law that enables reliable extrapolation of large-N attack success rates from small-budget measurements. Using only n=100 samples, our anchored estimator predicts ASR@1000 with a mean absolute error of 1.66, compared to 12.04 for the baseline, which is an 86.2% reduction in estimation error. Our results reveal heterogeneous risk scaling profiles and show that models appearing robust under standard evaluation can experience rapid nonlinear risk amplification under parallel adversarial pressure. This work provides a low-cost, scalable methodology for realistic LLM safety assessment. We will release our code and evaluation scripts upon publication to future research.