Evaluating Language Model Safety Across Long Adversarial Conversations

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.

Most adversarial evaluations of large language model (LLM) safety assess single prompts and report binary pass/fail outcomes, which fails to capture how safety properties evolve under sustained adversarial interaction. We present ADVERSA, an automated red-teaming framework that measures guardrail degradation dynamics as continuous per-round compliance trajectories rather than discrete jailbreak events. ADVERSA uses a fine-tuned 70B attacker model (ADVERSA-Red, Llama-3.1-70B-Instruct with QLoRA) that eliminates the attacker-side safety refusals that render off-the-shelf models unreliable as attackers, scoring victim responses on a structured 5-point rubric that treats partial compliance as a distinct measurable state. We report a controlled experiment across three frontier victim models (Claude Opus 4.6, Gemini 3.1 Pro, GPT-5.2) using a triple-judge consensus architecture in which judge reliability is measured as a first-class research outcome rather than assumed. Across 15 conversations of up to 10 adversarial rounds, we observe a 26.7% jailbreak rate with an average jailbreak round of 1.25, suggesting that in this evaluation setting, successful jailbreaks were concentrated in early rounds rather than accumulating through sustained pressure. We document inter-judge agreement rates, self-judge scoring tendencies, attacker drift as a failure mode in fine-tuned attackers deployed out of their training distribution, and attacker refusals as a previously-underreported confound in victim resistance measurement. All limitations are stated explicitly. Attack prompts are withheld per responsible disclosure policy; all other experimental artifacts are released.

Safety alignment in large language models is typically evaluated under isolated queries, yet real-world use is inherently multi-turn. Although multi-turn jailbreaks are empirically effective, the structure of conversational safety failure remains insufficiently understood. In this work, we study safety failures from a state-space perspective and show that many multi-turn safety failures in current safety-aligned language models arise from contextual state evolution, a regime that is not fully captured by isolated prompt-level analyses alone. We introduce STAR, a state-oriented diagnostic framework that treats dialogue history as a state transition operator and enables controlled analysis of safety behavior along interaction trajectories. Rather than optimizing attack strength, STAR provides a principled probe of how aligned models traverse the safety boundary under autoregressive conditioning. Across multiple frontier language models, we find that systems that appear robust under static evaluation can undergo rapid and reproducible safety collapse under structured multi-turn interaction. Mechanistic analysis reveals monotonic drift away from refusal-related representations and abrupt phase transitions induced by role-conditioned context. Together, these findings motivate viewing language model safety as a dynamic, state-dependent process defined over conversational trajectories.