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Jul 30

ContextualJailbreak: Evolutionary Red-Teaming via Simulated Conversational Priming

Large language models (LLMs) remain vulnerable to jailbreak attacks that bypass safety alignment and elicit harmful responses. A growing body of work shows that contextual priming, where earlier turns covertly bias later replies, constitutes a powerful attack surface, with hand-crafted multi-turn scaffolds consistently outperforming single-turn manipulations on capable models. However, automated optimization-based red-teaming has remained largely limited to the single-turn setting, iterating over static prompts and lacking the ability to reason about which forms of conversational priming induce compliance. While recent multi-turn, search-based approaches have begun to bridge this gap, the mutator design space underlying effective primed dialogues remains largely unexplored. We present ContextualJailbreak, a black-box red-teaming strategy that performs evolutionary search over a simulated multi-turn primed dialogue. The strategy leverages a graded 0-5 harm score from a two-level judge as an in-loop signal, enabling partially harmful responses to guide the search process rather than being discarded. Search is driven by five semantically defined mutation operators: roleplay, scenario, expand, troubleshooting, and mechanistic, of which the last two are novel contributions of this work. Across 50 representative HarmBench behaviors, ContextualJailbreak achieves an ASR of 100% on gpt-oss:20B, 100% on qwen3-8B, 100% on llama3.1:70B, and 90% on gpt-oss:120B, outperforming four single- and multi-turn baselines by 31-96 percentage points on average. The 40 maximally harmful attacks discovered against gpt-oss:120B transfer without adaptation to closed frontier models, achieving 90.0% on gpt-4o-mini, 70.0% on gpt-5, and 70.0% on gemini-3-flash, but only 17.5% on claude-opus-4-7 and 15.0% on claude-sonnet-4-6, revealing a pronounced provider-level asymmetry in alignment robustness.

  • 4 authors
·
May 3

How Reliable Is Your Jailbreak Judge? Calibration and Adversarial Robustness of Automated ASR Scoring

Almost every paper on LLM jailbreaks and prompt injection reports an attack-success rate (ASR), and that number is assigned not by people but by an automated judge: either a safety classifier trained for the task, or a general chat model prompted to grade. The judge is rarely checked. We check it. Using 596 human-labeled completions from the HarmBench classifier validation set, we compare the two judge families against human majority votes and then attack them. The two families fail in opposite ways. The dedicated classifier over-flags (precision 0.835, recall 0.974); three different LLM-as-judges keep high precision (0.81 to 0.94) but show erratic recall (0.06 to 0.65), so the same responses produce very different ASR depending on which judge scores them. The two families also differ sharply in robustness. Wrappers that leave the harmful text untouched and only add benign framing flip every LLM-judge between 57% and 100% of the time, and a single prepended refusal sentence accounts for much of this (39% to 88%). The dedicated classifier resists these surface attacks (at most 6.7%), but a white-box GCG attack on its open weights flips 70% of confident true positives (21 of 30; 95% CI 54 to 86%) even at a small optimization budget. A two-annotator audit confirms the attacks leave the harm intact: every one of 80 sampled flips still contained the harmful content. Because a large and growing share of reported ASR comes from LLM-judges, many such numbers are unreliable both on average and under deliberate pressure. We recommend that papers report judge precision and recall on a human-labeled slice, report ASR corrected for judge precision, and include an adversarial check of the judge. Our code is released.

  • 1 authors
·
Jun 24

DiffusionAttacker: Diffusion-Driven Prompt Manipulation for LLM Jailbreak

Large Language Models (LLMs) are susceptible to generating harmful content when prompted with carefully crafted inputs, a vulnerability known as LLM jailbreaking. As LLMs become more powerful, studying jailbreak methods is critical to enhancing security and aligning models with human values. Traditionally, jailbreak techniques have relied on suffix addition or prompt templates, but these methods suffer from limited attack diversity. This paper introduces DiffusionAttacker, an end-to-end generative approach for jailbreak rewriting inspired by diffusion models. Our method employs a sequence-to-sequence (seq2seq) text diffusion model as a generator, conditioning on the original prompt and guiding the denoising process with a novel attack loss. Unlike previous approaches that use autoregressive LLMs to generate jailbreak prompts, which limit the modification of already generated tokens and restrict the rewriting space, DiffusionAttacker utilizes a seq2seq diffusion model, allowing more flexible token modifications. This approach preserves the semantic content of the original prompt while producing harmful content. Additionally, we leverage the Gumbel-Softmax technique to make the sampling process from the diffusion model's output distribution differentiable, eliminating the need for iterative token search. Extensive experiments on Advbench and Harmbench demonstrate that DiffusionAttacker outperforms previous methods across various evaluation metrics, including attack success rate (ASR), fluency, and diversity.

  • 7 authors
·
Dec 23, 2024

RainbowPlus: Enhancing Adversarial Prompt Generation via Evolutionary Quality-Diversity Search

Large Language Models (LLMs) exhibit remarkable capabilities but are susceptible to adversarial prompts that exploit vulnerabilities to produce unsafe or biased outputs. Existing red-teaming methods often face scalability challenges, resource-intensive requirements, or limited diversity in attack strategies. We propose RainbowPlus, a novel red-teaming framework rooted in evolutionary computation, enhancing adversarial prompt generation through an adaptive quality-diversity (QD) search that extends classical evolutionary algorithms like MAP-Elites with innovations tailored for language models. By employing a multi-element archive to store diverse high-quality prompts and a comprehensive fitness function to evaluate multiple prompts concurrently, RainbowPlus overcomes the constraints of single-prompt archives and pairwise comparisons in prior QD methods like Rainbow Teaming. Experiments comparing RainbowPlus to QD methods across six benchmark datasets and four open-source LLMs demonstrate superior attack success rate (ASR) and diversity (Diverse-Score approx 0.84), generating up to 100 times more unique prompts (e.g., 10,418 vs. 100 for Ministral-8B-Instruct-2410). Against nine state-of-the-art methods on the HarmBench dataset with twelve LLMs (ten open-source, two closed-source), RainbowPlus achieves an average ASR of 81.1%, surpassing AutoDAN-Turbo by 3.9%, and is 9 times faster (1.45 vs. 13.50 hours). Our open-source implementation fosters further advancements in LLM safety, offering a scalable tool for vulnerability assessment. Code and resources are publicly available at https://github.com/knoveleng/rainbowplus, supporting reproducibility and future research in LLM red-teaming.

knoveleng Knovel Engineering
·
Apr 21, 2025 13

A Mousetrap: Fooling Large Reasoning Models for Jailbreak with Chain of Iterative Chaos

Large Reasoning Models (LRMs) have significantly advanced beyond traditional Large Language Models (LLMs) with their exceptional logical reasoning capabilities, yet these improvements introduce heightened safety risks. When subjected to jailbreak attacks, their ability to generate more targeted and organized content can lead to greater harm. Although some studies claim that reasoning enables safer LRMs against existing LLM attacks, they overlook the inherent flaws within the reasoning process itself. To address this gap, we propose the first jailbreak attack targeting LRMs, exploiting their unique vulnerabilities stemming from the advanced reasoning capabilities. Specifically, we introduce a Chaos Machine, a novel component to transform attack prompts with diverse one-to-one mappings. The chaos mappings iteratively generated by the machine are embedded into the reasoning chain, which strengthens the variability and complexity and also promotes a more robust attack. Based on this, we construct the Mousetrap framework, which makes attacks projected into nonlinear-like low sample spaces with mismatched generalization enhanced. Also, due to the more competing objectives, LRMs gradually maintain the inertia of unpredictable iterative reasoning and fall into our trap. Success rates of the Mousetrap attacking o1-mini, Claude-Sonnet and Gemini-Thinking are as high as 96%, 86% and 98% respectively on our toxic dataset Trotter. On benchmarks such as AdvBench, StrongREJECT, and HarmBench, attacking Claude-Sonnet, well-known for its safety, Mousetrap can astonishingly achieve success rates of 87.5%, 86.58% and 93.13% respectively. Attention: This paper contains inappropriate, offensive and harmful content.

  • 8 authors
·
Feb 19, 2025

AutoRedTeamer: Autonomous Red Teaming with Lifelong Attack Integration

As large language models (LLMs) become increasingly capable, security and safety evaluation are crucial. While current red teaming approaches have made strides in assessing LLM vulnerabilities, they often rely heavily on human input and lack comprehensive coverage of emerging attack vectors. This paper introduces AutoRedTeamer, a novel framework for fully automated, end-to-end red teaming against LLMs. AutoRedTeamer combines a multi-agent architecture with a memory-guided attack selection mechanism to enable continuous discovery and integration of new attack vectors. The dual-agent framework consists of a red teaming agent that can operate from high-level risk categories alone to generate and execute test cases and a strategy proposer agent that autonomously discovers and implements new attacks by analyzing recent research. This modular design allows AutoRedTeamer to adapt to emerging threats while maintaining strong performance on existing attack vectors. We demonstrate AutoRedTeamer's effectiveness across diverse evaluation settings, achieving 20% higher attack success rates on HarmBench against Llama-3.1-70B while reducing computational costs by 46% compared to existing approaches. AutoRedTeamer also matches the diversity of human-curated benchmarks in generating test cases, providing a comprehensive, scalable, and continuously evolving framework for evaluating the security of AI systems.

  • 10 authors
·
Mar 19, 2025

Refusal-Trained LLMs Are Easily Jailbroken As Browser Agents

For safety reasons, large language models (LLMs) are trained to refuse harmful user instructions, such as assisting dangerous activities. We study an open question in this work: does the desired safety refusal, typically enforced in chat contexts, generalize to non-chat and agentic use cases? Unlike chatbots, LLM agents equipped with general-purpose tools, such as web browsers and mobile devices, can directly influence the real world, making it even more crucial to refuse harmful instructions. In this work, we primarily focus on red-teaming browser agents, LLMs that manipulate information via web browsers. To this end, we introduce Browser Agent Red teaming Toolkit (BrowserART), a comprehensive test suite designed specifically for red-teaming browser agents. BrowserART is consist of 100 diverse browser-related harmful behaviors (including original behaviors and ones sourced from HarmBench [Mazeika et al., 2024] and AirBench 2024 [Zeng et al., 2024b]) across both synthetic and real websites. Our empirical study on state-of-the-art browser agents reveals that, while the backbone LLM refuses harmful instructions as a chatbot, the corresponding agent does not. Moreover, attack methods designed to jailbreak refusal-trained LLMs in the chat settings transfer effectively to browser agents. With human rewrites, GPT-4o and o1-preview-based browser agents attempted 98 and 63 harmful behaviors (out of 100), respectively. We publicly release BrowserART and call on LLM developers, policymakers, and agent developers to collaborate on improving agent safety

  • 12 authors
·
Oct 11, 2024

Jailbreaking Leading Safety-Aligned LLMs with Simple Adaptive Attacks

We show that even the most recent safety-aligned LLMs are not robust to simple adaptive jailbreaking attacks. First, we demonstrate how to successfully leverage access to logprobs for jailbreaking: we initially design an adversarial prompt template (sometimes adapted to the target LLM), and then we apply random search on a suffix to maximize the target logprob (e.g., of the token "Sure"), potentially with multiple restarts. In this way, we achieve nearly 100\% attack success rate -- according to GPT-4 as a judge -- on GPT-3.5/4, Llama-2-Chat-7B/13B/70B, Gemma-7B, and R2D2 from HarmBench that was adversarially trained against the GCG attack. We also show how to jailbreak all Claude models -- that do not expose logprobs -- via either a transfer or prefilling attack with 100\% success rate. In addition, we show how to use random search on a restricted set of tokens for finding trojan strings in poisoned models -- a task that shares many similarities with jailbreaking -- which is the algorithm that brought us the first place in the SaTML'24 Trojan Detection Competition. The common theme behind these attacks is that adaptivity is crucial: different models are vulnerable to different prompting templates (e.g., R2D2 is very sensitive to in-context learning prompts), some models have unique vulnerabilities based on their APIs (e.g., prefilling for Claude), and in some settings it is crucial to restrict the token search space based on prior knowledge (e.g., for trojan detection). We provide the code, prompts, and logs of the attacks at https://github.com/tml-epfl/llm-adaptive-attacks.

  • 3 authors
·
Apr 2, 2024

CausalRM: Causal-Theoretic Reward Modeling for RLHF from Observational User Feedbacks

Despite the success of reinforcement learning from human feedback (RLHF) in aligning language models, current reward modeling heavily relies on experimental feedback data collected from human annotators under controlled and costly conditions. In this work, we introduce observational reward modeling -- learning reward models with observational user feedback (e.g., clicks, copies, and upvotes) -- as a scalable and cost-effective alternative. We identify two fundamental challenges in this setting: (1) observational feedback is noisy due to annotation errors, which deviates it from true user preference; (2) observational feedback is biased by user preference, where users preferentially provide feedback on responses they feel strongly about, which creats a distribution shift between training and inference data. To address these challenges, we propose CausalRM, a causal-theoretic reward modeling framework that aims to learn unbiased reward models from observational feedback. To tackle challenge (1), CausalRM introduces a noise-aware surrogate loss term that is provably equivalent to the primal loss under noise-free conditions by explicitly modeling the annotation error generation process. To tackle challenge (2), CausalRM uses propensity scores -- the probability of a user providing feedback for a given response -- to reweight training samples, yielding a loss function that eliminates user preference bias. Extensive experiments across diverse LLM backbones and benchmark datasets validate that CausalRM effectively learns accurate reward signals from noisy and biased observational feedback and delivers substantial performance improvements on downstream RLHF tasks -- including a 49.2% gain on WildGuardMix and a 32.7% improvement on HarmBench. Code is available on our project website.

  • 10 authors
·
Mar 19