State-Dependent Safety Failures in Multi-Turn Language Model Interaction

Large language models (LLMs) are vulnerable to multi-turn jailbreak attacks that progressively manipulate conversation context. Existing certified robustness methods are limited to single-turn inputs; naive multi-turn composition yields bounds that degrade exponentially in the number of turns. We introduce Multi-Turn Certified Robustness (MTCR), a framework that models conversational safety via State-Adversarial MDPs and defines $k$-turn certified robustness as the worst-case safety probability across $k$ adversarial turns. MTCR comprises: (i) compositional certification via embedding-space mode decomposition, yielding tighter certified lower bounds than naive multiplication; (ii) $(α,β)$-safety persistence, improving the degradation rate from $\underline{p}^{k}$ to $β^k$ (with $β> \underline{p}$) and yielding interpretable horizon estimates; (iii) matching information-theoretic upper bounds establishing tightness; and (iv) a unified algorithm combining these results. Experiments on six LLMs under $ε$-bounded and Crescendo-style attacks confirm that empirical safety consistently exceeds the certified bounds.

As Large Language Models (LLMs) move from conversational assistants to advanced agentic systems, guardrail failures can convert adversarial intents into harmful executions. However, most evaluation frameworks focus only on whether a user request is unsafe. This is insufficient for multi-turn failures, where adversarial intent may be distributed across turns and emerge only from accumulated context. This motivates us to go beyond detection to localize the evidence that pushes the conversation toward unsafe trajectories. We introduce MTAG-Bench, a multi-turn guardrail attribution dataset with behavioral validation and counterfactual supervision containing 4,167 conversations. We also introduce MTAG-Probe, a hierarchical attribution model for turn- and span-level evidence localization with conversation-level safety detection. MTAG-Probe improves turn-level F1 by 28.1 and 24.1 points (79.0% and 61.0% relative) over self-attribution by the model that produced the unsafe response and the LLM safety-judge attribution, respectively. Removing MTAG-Probe's top-ranked evidence within budgets of 15% and 20% of user words per conversation changes 50.6% and 60.8% of Llama Guard decisions on Geometry from unsafe to safe, respectively. In full-trajectory replay, MTAG-Probe converts 84.3% of eligible unsafe final responses to safe. These results show that MTAG-Probe can provide evidence-level explanations as a practical complement to safety detection.

Conversational safety evaluations often test language models with a single harmful prompt, even though real-world systems interact with users through long, adaptive conversations. This study examines whether models continue to respond safely when an adversarial user persists across multiple turns. We evaluate three open-weight, instruction-tuned models on two harmful prompts across different conversation lengths and random seeds. In each setting, a second language model acts as a persistent adversarial user, while a safety classifier labels every response as safe or unsafe. Across all model-prompt combinations, first-turn safe-response rates ranged from 85% to 100%. By depth 11, they dropped to 38-61%, and by depth 101, to 15-44%. This decline appeared across models and continued well beyond the short interactions typically used in multi-turn safety evaluations. These results provide proof-of-concept evidence that strong single-turn safety does not necessarily persist during sustained adversarial interaction. They highlight the need for long-horizon evaluations and conversation-level safeguards that account for risk accumulating across turns.