Frontier language models that refuse harmful single-turn prompts often comply when the same intent is reached gradually over many turns, making multi-turn attacks one of the least understood failure modes of large language models. Most automated red-teaming methods treat this as a generation problem: produce attacks that break the model. We argue it is better framed as a search problem: discover, organize, and iteratively refine a diverse archive of attack strategies, producing a structured map of how a target model fails rather than a list of one-off successes. We introduce EvoFlint, which applies evolutionary quality-diversity search to multi-turn red-teaming. Attack strategies are phased conversation plans, not raw prompts, and are evolved through LLM-driven mutation and crossover. A Pareto fitness over attack success rate and peak severity preserves selection signal from near-miss attacks. A risk-indexed archive runs novelty search with local competition over strategy description embeddings inside each cell, maintaining diversity without committing to a predefined style taxonomy. A generation-level memory accumulates target-model insights across the population and feeds them back into strategy generation. On the HarmBench-test split, EvoFlint reaches attack success rates of 35.8% on Claude Sonnet 4.6, 59.7% on GPT-5.4, and 94.3% on Qwen3-32B, alongside 98.7% on the older GPT-4o included as a baseline reference. The resulting archive, organized by risk category, exposes for each target which categories of harm its safety training has and has not covered.
Multi-turn jailbreak attacks have emerged as a critical safety threat to LLMs, as harmful objectives are decomposed across a sequence of apparently benign turns to bypass guardrails. Existing defenses lack the reasoning capacity to identify evolving manipulation patterns, often trading helpfulness for safety by over-refusing benign requests related to sensitive topics. We introduce Trace, a multi-turn defense with trajectory-aware structured reasoning. Before generating each response, the model identifies manipulation cues from the trajectory, evaluates both the benign and adversarial interpretations of user intent, assigns a jailbreak score, and commits to an action: Allow, Caution, or Decline. We curate 4k multi-turn adversarial conversations from five attack frameworks, pair them with 2.4k benign dialogs, and 600 sensitive-but-benign conversations. We train Llama-3.1-8B-Instruct with SFT and GRPO under a multi-component reward that jointly optimizes helpfulness on benign prompts and robustness against jailbreak attempts. Across seven multi-turn attack benchmarks, Trace attains an average attack success rate (ASR) of 14.5% against 31.4% for the strongest baseline and 74.9% for the undefended target, while significantly raising the attacker effort required per successful jailbreak. Trace also balances usability and safety, achieving a 93.3% average compliance on over-refusal benchmarks.
Devina Jain, David Hartmann, Chuan Lics.CR cs.AI cs.LG
LLM-based agents process external content, exposing them to prompt injection and multi-turn manipulation. Most safety benchmarks evaluate defenders against fixed attack pools collected before evaluation, single-turn or multi-turn. We present a 21-scenario benchmark for \emph{adaptive multi-round attacks against memoryless LLM defenders}: an autonomous LLM attacker observes prior defender responses and pivots across rounds, while each defender response is evaluated as a fresh interaction. Holding the 21 scenarios, attackers, defenders, and structured-output scoring fixed, restricting scoring to the first attacker turn yields $0$-$1\%$ attack success rate (ASR); allowing 15 rounds of adaptive attack yields $5.4$-$14.0\%$. Pooling three frontier attacker LLMs uncovers $1.4$-$2.2\times$ as many unique successful attacks as the best single attacker, and the generated attacks have low cosine similarity ($0.02$-$0.14$) to attacks in existing benchmarks. Claude Opus 4.6 and GPT-5.4 are tied in aggregate ($5.4\%$ each; overlapping $95\%$ CIs), but their weaknesses differ sharply: on one scenario Opus reaches $60\%$ ASR ($95\%$ CI $36$--$80\%$) while GPT-5.4 and Gemini each stay at $7\%$ (CI $1$-$30\%$; the gap is preserved in a higher-$N$ replication). $13$ of $21$ scenarios distinguish at least one defender pair, yet rankings disagree across scenarios (Kendall's $W = 0.19$). We release the benchmark -- 21 evaluation scenarios, 10 public development scenarios, the orchestrator, baseline harnesses, and a multi-attacker CLI -- plus 945 transcripts from the 3$\times$3 frontier matrix, an attack-replay dataset, and 18{,}422 gpt-oss-20b battles from an open competition's final scoring rounds.
Hanwool Lee, Dasol Choi, Bokyeong Kim +2cs.CR cs.AI
Large language model (LLM) agents are increasingly proposed as supervisory components for safety-critical systems, yet their robustness under sustained, adaptive adversarial pressure remains poorly characterized. We present NRT-Bench, a benchmark for multi-turn red-teaming of LLM agents acting as operators of a safety-critical system, instantiated in a simulated nuclear power plant control room. A five-role operator team, each backed by a configurable LLM, runs a plant governed by six critical safety functions (CSFs), while adversaries inject messages over four channels in bounded multi-turn sessions with per-turn feedback. Harm is an objective signal rather than LLM-judged text: a run terminates the moment any CSF is lost, attributed to the causing message. Evaluating four frontier operator models under a fixed-attack paired-replay protocol, we find that adaptive multi-turn attacks reliably push the operator team past a safety limit: across the four models, between 8.7% and 12.1% of attack sessions end with the plant losing a critical safety function. Although the four models look almost equally robust by this aggregate rate, their failures barely overlap: of $149$ sessions, none defeat all four models while a third defeat at least one, so vulnerabilities are nearly disjoint across models rather than nested. The effect of added defences is strongly model-dependent: the same guardrail stack or safety-advisor agent that lowers attack success for one model can raise it for another. We release the simulation venue, attack dataset, and replay tooling for reproducible safety evaluation of LLM agents.
Multi-turn jailbreak attacks on large language models (LLMs) reveal a mismatch in current guardrails: they operate on individual turns, while attacks unfold as trajectories across conversations. We propose a shift from content to dynamics, modeling conversations as paths in representation space and asking whether adversarial intent is encoded early in their geometry. We introduce PsychoPass, a framework that extracts geometric features from conversation trajectories in embedding space to predict a potential attack before harmful content is produced. These features achieve near-perfect performance in naïve classifiers, which is largely explained by the inclusion of number of turns as a feature. After removing this confound, a smaller but consistent geometric signal remains, with classification performance that does not depend meaningfully on encoder choice. Crucially, this signal appears early in the conversation: attack outcomes remain above chance from short prefixes alone, more reliably than baseline guardrails. A supporting theoretical analysis explains these findings via a decomposition of length and shape, a detection bound based on prefix length, and encoder invariance. Together, these results show that adversarial conversations leave an early, representation-robust geometric fingerprint suitable for online monitoring.
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.
Multi-turn prompt injection follows a known attack path -- trust-building, pivoting, escalation but text-level defenses miss covert attacks where individual turns appear benign. We show this attack path leaves an activation-level signature in the model's residual stream: each phase shift moves the activation, producing a total path length far exceeding benign conversations. We call this adversarial restlessness. Five scalar trajectory features capturing this signal lift conversation-level detection from 76.2% to 93.8% on synthetic held-out data. The signal replicates across four model families (24B-70B); probes are model-specific and do not transfer across architectures. Generalization is source-dependent: leave-one-source-out evaluation shows each of synthetic, LMSYS-Chat-1M, and SafeDialBench captures distinct attack distributions, with detection on real-world LMSYS reaching 47-71% when its distribution is represented in training. Combined three-source training achieves 89.4% detection at 2.4% false positive rate on a held-out mixed set. We further show that three-phase turn-level labels(benign/pivoting/adversarial) unique to our synthetic dataset are essential: binary conversation-level labels produce 50-59% false positives. These results establish adversarial restlessness as a reliable activation-level signal and characterize the data requirements for practical deployment.