How Many Iterations to Jailbreak? Dynamic Budget Allocation for Multi-Turn LLM Evaluation

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.

Modern large language models (LLMs) operate in interactive multi-turn settings, making multi-turn jailbreaking a realistic threat model and an important setting for automated red teaming. A core challenge in learning multi-turn jailbreak attackers is credit assignment: different turns contribute differently to the final outcome, yet existing learning signals are often too coarse to identify their individual contributions. We propose decomposed credit GRPO (DC-GRPO), a unified turn-level credit assignment framework for Group Relative Policy Optimization in multi-turn jailbreak learning. DC-GRPO assigns a separate group-relative learning signal to each turn by combining immediate and future credit, avoiding the credit misassignment induced by broadcasting a single trajectory-level score across the dialogue. We instantiate this framework with static and dynamic weighting rules that differ in how the two credit sources are balanced while sharing the same turn-level structure. Across multiple victim LLMs and benchmarks, the dynamic- and static-weighted variants achieve average ASR5@3 scores of 98.26% and 97.88%, respectively, substantially outperforming the state-of-the-art methods, including SEMA (86.58%) and TROJail (86.23%). Their consistently strong performance indicates that the central empirical benefit comes from turn-level group-relative credit assignment rather than a particular weighting rule. Warning: This paper contains examples of harmful content.

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.