DeepContext: Stateful Real-Time Detection of Multi-Turn Adversarial Intent Drift in LLMs

Large language models (LLMs) are increasingly integrated into sensitive workflows, raising the stakes for adversarial robustness and safety. This paper introduces Transient Turn Injection(TTI), a new multi-turn attack technique that systematically exploits stateless moderation by distributing adversarial intent across isolated interactions. TTI leverages automated attacker agents powered by large language models to iteratively test and evade policy enforcement in both commercial and open-source LLMs, marking a departure from conventional jailbreak approaches that typically depend on maintaining persistent conversational context. Our extensive evaluation across state-of-the-art models-including those from OpenAI, Anthropic, Google Gemini, Meta, and prominent open-source alternatives-uncovers significant variations in resilience to TTI attacks, with only select architectures exhibiting substantial inherent robustness. Our automated blackbox evaluation framework also uncovers previously unknown model specific vulnerabilities and attack surface patterns, especially within medical and high stakes domains. We further compare TTI against established adversarial prompting methods and detail practical mitigation strategies, such as session level context aggregation and deep alignment approaches. Our study underscores the urgent need for holistic, context aware defenses and continuous adversarial testing to future proof LLM deployments against evolving multi-turn threats.

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.

Hidden malicious intent in multi-turn dialogue poses a growing threat to deployed large language models (LLMs). Rather than exposing a harmful objective in a single prompt, attackers can distribute their intent across multiple benign-looking turns, making defense a problem not only of whether a dialogue is harmful, but also of when intervention becomes necessary. Existing trace-level labeling approaches provide only coarse safety signals and do not identify this intervention boundary, making it difficult to distinguish timely intervention from premature refusal or a block that comes too late. This work introduces turn-level harm-enabling supervision for multi-turn defense. We define the earliest harm-enabling turn as the first point at which delivering a candidate response would make the accumulated interaction sufficient to enable harmful action. To instantiate this supervision at scale, we construct the Multi-Turn Intent Dataset (MTID), which contains adaptive attack rollouts, matched benign hard negatives, and annotations of this boundary. Using MTID, we train TurnGate, a response-aware monitor that learns when to intervene, and further optimize its policy through multi-turn reinforcement learning. Experiments show that turn-level boundary supervision improves intervention localization, while reinforcement learning further improves the safety--utility trade-off. TurnGate outperforms existing guardrails and multi-turn monitoring baselines, and generalizes across risk domains, attacker pipelines, and target models. Our code is available at https://github.com/Graph-COM/TurnGate.