Jailbreak Attacks

Deploying LLMs in multi-turn dialogues facilitates jailbreak attacks that distribute harmful intent across seemingly benign turns. Recent training-based multi-turn jailbreak methods learn long-horizon attack strategies from interaction feedback, but often rely on coarse trajectory-level outcome signals that broadcast uniformly to every turn. However, we find that turn-level contributions in multi-turn jailbreaking are non-uniform, phase-dependent, and target-specific. Such coarse outcome supervision induces a credit assignment problem, leading to over-rewarding redundant turns in successful trajectories and under-crediting useful intermediate turns in failed ones. To address this, we propose TRACE, a turn-aware credit assignment framework for reinforcement learning (RL)-based multi-turn jailbreaking. For successful trajectories, TRACE estimates turn-level contributions via leave-one-turn-out semantic masking; for failed ones, TRACE assigns penalties based on prompt harmfulness and semantic relevance, with an additional local refusal-aware penalty. Furthermore, we reuse the attack-side credit signal for multi-turn defense alignment. Extensive experiments on open-source and closed-source targets show that TRACE achieves strong overall performance in effectiveness, transferability, and efficiency, yielding about a 25% relative improvement in attack success rate over the strongest RL baseline while also improving the safety-utility balance when reused for defense alignment.

Many-shot jailbreaking (MSJ) causes safety-aligned language models to answer harmful queries by preceding them with many harmful question-answer demonstrations. We study why this attack becomes stronger as the number of demonstrations increases. Empirically, we find that MSJ induces a progressive activation drift: the representation of a fixed harmful query moves step by step away from the safety-aligned region as more harmful demonstrations are added. Theoretically, we show that this drift can be interpreted as implicit malicious fine-tuning: conditioning on N harmful demonstrations induces SGD-style updates equivalent to optimizing on the corresponding N harmful samples. This view turns the attack mechanism into a defense principle. We append a fixed one-shot safety demonstration at inference time, which induces a counteracting safety-oriented update and restores refusal behavior. The resulting method improves the model's robustness to MSJ without modifying its parameters or requiring white-box access at deployment. Code is available at https://github.com/Thecommonirin/SafeEnd.

Intent-obfuscation-based jailbreak attacks on multimodal large language models (MLLMs) transform a harmful query into a concealed multimodal input to bypass safety mechanisms. We show that such attacks are governed by a \emph{reconstruction--concealment tradeoff}: the transformed input must hide harmful intent from safety filters while remaining recoverable enough for the victim model to reconstruct the original request. Through a reconstruction analysis of three representative black-box methods, we find that existing transformations struggle to balance this tradeoff, limiting their effectiveness. In contrast, we show that character-removed variants achieve a better balance. Building on this, we propose \emph{concealment-aware variant construction}, which greedily selects character-removed variants that are low in harmful-keyword alignment and mutually diverse, and instantiates them through five modality-aware prompting strategies. We further introduce \emph{keyword-related distractor images} that depict the harmful keyword in diverse contexts, providing more effective auxiliary visual context than generic distractor images. Experiments across closed-source and open-source MLLMs show the proposed strategies outperform strong baselines, revealing an underexplored vulnerability: a model's own reconstruction ability can be exploited to recover hidden harmful intent and produce unsafe responses.

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.

We present MultiBreak, a scalable and diverse multi-turn jailbreak benchmark to evaluate large language model (LLM) safety. Multi-turn jailbreaks mimic natural conversational settings, making them easier to bypass safety-aligned LLM than single-turn jailbreaks. Existing multi-turn benchmarks are limited in size or rely heavily on templates, which restrict their diversity. To address this gap, we unify a wide range of harmful jailbreak intents, and introduce an active learning pipeline for expanding high-quality multi-turn adversarial prompts, where a generator is iteratively fine-tuned to produce stronger attack candidates, guided by uncertainty-based refinement. Our MultiBreak includes 10,389 multi-turn adversarial prompts, spans 2,665 distinct harmful intents, and covers the most diverse set of topics to date. Empirical evaluation shows that our benchmark achieves up to a 54.0 and 34.6 higher attack success rate (ASR)} than the second-best dataset on DeepSeek-R1-7B and GPT-4.1-mini, respectively. More importantly, safety evaluations suggest that diverse attack categories uncover fine-grained LLM vulnerabilities}, and categories that appear benign under single-turn can exhibit substantially higher adversarial effectiveness in multi-turn scenarios. These findings highlight persistent vulnerabilities of LLMs under realistic adversarial settings and establish MultiBreak as a scalable resource for advancing LLM safety.

As language model safeguards become more robust, attackers are pushed toward developing increasingly complex jailbreaks. Prior work has found that this complexity imposes a "jailbreak tax" that degrades the target model's task performance. We show that this tax scales inversely with model capability and that the most advanced jailbreaks effectively yield no reduction in model capabilities. Evaluating 28 jailbreaks on five benchmarks across Claude models ranging in capability from Haiku 4.5 to Opus 4.6, we find Haiku 4.5 loses an average of 33.1% on benchmark performance when jailbroken, while Opus 4.6 at max thinking effort loses only 7.7%. We also observe that across all models, reasoning-heavy tasks display considerably more degradation than knowledge-recall tasks. Finally, Boundary Point Jailbreaking, currently the strongest jailbreak against deployed classifiers, achieves near-perfect classifier evasion with near-zero degradation across safeguarded models. We recommend that safety cases for frontier models should not rely on a meaningful capability degradation from jailbreaks.

Decompositional jailbreaks pose a critical threat to large language models (LLMs) by allowing adversaries to fragment a malicious objective into a sequence of individually benign queries that collectively reconstruct prohibited content. In real-world deployments, LLMs face a continuous, untraceable stream of fully anonymized and arbitrarily interleaved requests, infiltrated by covertly distributed adversarial queries. Under this rigorous threat model, state-of-the-art defensive strategies exhibit fundamental limitations. In the absence of trustworthy user metadata, they are incapable of tracking global historical contexts, while their deployment of generative models for real-time monitoring introduces computationally prohibitive overhead. To address this, we present TwinGate, a stateful dual-encoder defense framework. TwinGate employs Asymmetric Contrastive Learning (ACL) to cluster semantically disparate but intent-matched malicious fragments in a shared latent space, while a parallel frozen encoder suppresses false positives arising from benign topical overlap. Each request requires only a single lightweight forward pass, enabling the defense to execute in parallel with the target model's prefill phase at negligible latency overhead. To evaluate our approach and advance future research, we construct a comprehensive dataset of over 3.62 million instructions spanning 8,600 distinct malicious intents. Evaluated on this large-scale corpus under a strictly causal protocol, TwinGate achieves high malicious intent recall at a remarkably low false positive rate while remaining highly robust against adaptive attacks. Furthermore, our proposal substantially outperforms stateful and stateless baselines, delivering superior throughput and reduced latency.

Existing white-box jailbreak attacks against aligned LLMs typically append discrete adversarial suffixes to the user prompt, which visibly alters the prompt and operates in a combinatorial token space. Prior work has avoided directly optimizing the embeddings of the original prompt tokens, presumably because perturbing them risks destroying the prompt's semantic content. We propose Prompt Embedding Optimization (PEO), a multi-round white-box jailbreak that directly optimizes the embeddings of the original prompt tokens without appending any adversarial tokens, and show that the concern is unfounded: the optimized embeddings remain close enough to their originals that the visible prompt string is preserved exactly after nearest-token projection, and quantitative analysis shows the model's responses stay on topic for the large majority of prompts. PEO combines continuous embedding-space optimization with structured continuation targets and an adaptive failure-focused schedule. Counterintuitively, later PEO rounds can benefit from heuristic composite response scaffolds that are not natural standalone templates, yet ASR-Judge shows that the resulting gains are not merely empty formatting or scaffold-only outputs. Across two standard harmful-behavior benchmarks and competing white-box attacks spanning discrete suffix search, appended adversarial embeddings, and search-based adversarial generation, PEO outperforms all of them in our experiments.

Large (vision-)language models exhibit remarkable capability but remain highly susceptible to jailbreaking. Existing safety training approaches aim to have the model learn a refusal boundary between safe and unsafe, based on the user's intent. It has been found that this binary training regime often leads to brittleness, since the user intent cannot reliably be evaluated, especially if the attacker obfuscates their intent, and also makes the system seem unhelpful. In response, frontier models, such as GPT-5, have shifted from refusal-based safeguards to safe completion, that aims to maximize helpfulness while obeying safety constraints. However, safe completion could be exploited when a user pretends their intention is benign. Specifically, this intent inversion would be effective in multi-turn conversation, where the attacker has multiple opportunities to reinforce their deceptively benign intent. In this work, we introduce a novel multi-turn jailbreaking method that exploits this vulnerability. Our approach gradually builds conversational trust by simulating benign-seeming intentions and by exploiting the consistency property of the model, ultimately guiding the target model toward harmful, detailed outputs. Most crucially, our approach also uncovered an additional class of model vulnerability that we call para-jailbreaking that has been unnoticed up to now. Para-jailbreaking describes the situation where the model may not reveal harmful direct reply to the attack query, however the information that it reveals is nevertheless harmful. Our contributions are threefold. First, it achieves high success rates against frontier models including GPT-5-thinking and Claude-Sonnet-4.5. Second, our approach revealed and addressed para-jailbreaking harmful output. Third, experiments on multimodal VLM models showed that our approach outperformed state-of-the-art models.

Automated red-teaming methods for large language models typically optimize attack prompts within a fixed, human-designed strategy, leaving the attack strategy itself unchanged. We instead optimize the strategy. We propose AutoRISE, a method that searches over executable attack programs rather than individual prompts. At each iteration, a coding agent edits a strategy and a fixed evaluation harness scores the resulting attacks, returning both a scalar objective and per-example diagnostics that guide subsequent edits. This allows structural changes, including new attack components and altered control flow, that prompt-level methods do not directly express. We also release two benchmark suites developed on disjoint target sets and evaluate on 11 models from five families against seven established jailbreak datasets. Across held-out models, AutoRISE improves average attack success rate by 17.0 points over the strongest baseline, and improves attack success by up to 16 points on frontier targets with low baseline success rates. Ablations against parametric and strategy-library baselines suggest that these gains arise from unrestricted program search, particularly compositional techniques and control-flow edits. AutoRISE operates in a black-box, inference-only setting, requiring no fine-tuning, human annotation, or GPU compute.

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.

The Adversarial Humanities Benchmark (AHB) evaluates whether model safety refusals survive a shift away from familiar harmful prompt forms. Starting from harmful tasks drawn from MLCommons AILuminate, the benchmark rewrites the same objectives through humanities-style transformations while preserving intent. This extends literature on Adversarial Poetry and Adversarial Tales from single jailbreak operators to a broader benchmark family of stylistic obfuscation and goal concealment. In the benchmark results reported here, the original attacks record 3.84% attack success rate (ASR), while transformed methods range from 36.8% to 65.0%, yielding 55.75% overall ASR across 31 frontier models. Under a European Union AI Act Code-of-Practice-inspired systemic-risk lens, Chemical, biological, radiological and nuclear (CBRN) is the highest bucket. Taken together, this lack of stylistic robustness suggests that current safety techniques suffer from weak generalization: deep understanding of 'non-maleficence' remains a central unresolved problem in frontier model safety.

Large Reasoning Models (LRMs) have demonstrated strong capabilities in generating step-by-step reasoning chains alongside final answers, enabling their deployment in high-stakes domains such as healthcare and education. While prior jailbreak attack studies have focused on the safety of final answers, little attention has been given to the safety of the reasoning process. In this work, we identify a novel problem that injects harmful content into the reasoning steps while preserving unchanged answers. This type of attack presents two key challenges: 1) manipulating the input instructions may inadvertently alter the LRM's final answer, and 2) the diversity of input questions makes it difficult to consistently bypass the LRM's safety alignment mechanisms and embed harmful content into its reasoning process. To address these challenges, we propose the Psychology-based Reasoning-targeted Jailbreak Attack (PRJA) Framework, which integrates a Semantic-based Trigger Selection module and a Psychology-based Instruction Generation module. Specifically, the proposed PRJA automatically selects manipulative reasoning triggers via semantic analysis and leverages psychological theories of obedience to authority and moral disengagement to generate adaptive instructions for enhancing the LRM's compliance with harmful content generation. Extensive experiments on five question-answering datasets demonstrate that PRJA achieves an average attack success rate of 83.6% against several commercial LRMs, including DeepSeek R1, Qwen2.5-Max, and OpenAI o4-mini.

Safety evaluation of multimodal large language models requires tracking not only whether an attack succeeds, but also how the interaction unfolds across turns and input modalities. We present MUSE (Multimodal Unified Safety Evaluation), an open-source, browser-based, run-centric platform for multimodal safety evaluation. MUSE treats each attack run as the persistent unit of execution, inspection, and analysis, preserving its configuration, multi-turn trajectory, delivered modalities and media, target responses, and safety judgments. A five-level response taxonomy further distinguishes full Compliance from Partial Compliance and refusal behavior, yielding hard ASR, soft ASR, and gray-zone width (GZW). Across 11,700 evaluations on six multimodal LLMs, direct text-only requests yield only 3.1% macro hard ASR and 4.4% soft ASR, while iterative attack procedures are substantially more effective. Attack effectiveness also varies substantially with the attacker backbone. In contrast, Inter-Turn Modality Switching (ITMS), evaluated as a controlled delivery-modality probe, does not consistently increase attack success. These results demonstrate the value of run-centric, fine-grained evaluation for characterizing multimodal safety behavior beyond a single binary success metric.

Recent advances in large image editing models have shifted the paradigm from text-driven instructions to vision-prompt editing, where user intent is inferred directly from visual inputs such as marks, arrows, and visual-text prompts. While this paradigm greatly expands usability, it also introduces a critical and underexplored safety risk: the attack surface itself becomes visual. In this work, we propose Vision-Centric Jailbreak Attack (VJA), the first visual-to-visual jailbreak attack that conveys malicious instructions purely through visual inputs. To systematically study this emerging threat, we introduce IESBench, a safety-oriented benchmark for image editing models. Extensive experiments on IESBench demonstrate that VJA effectively compromises state-of-the-art commercial models, achieving attack success rates of up to 80.9% on Nano Banana Pro and 70.1% on GPT-Image-1.5. To mitigate this vulnerability, we propose a training-free defense based on introspective multimodal reasoning, which substantially improves the safety of poorly aligned models to a level comparable with commercial systems, without auxiliary guard models and with negligible computational overhead. Our findings expose new vulnerabilities, provide both a benchmark and practical defense to advance safe and trustworthy modern image editing systems. Warning: This paper contains offensive images created by large image editing models.

Existing gradient-based jailbreak attacks on Large Language Models (LLMs) typically optimize adversarial suffixes to align the LLM output with predefined target responses. However, restricting the objective as inducing fixed targets inherently constrains the adversarial search space, limiting the overall attack efficacy. Furthermore, existing methods typically require numerous optimization iterations to fulfill the large gap between the fixed target and the original LLM output, resulting in low attack efficiency. To overcome these limitations, we propose NonTextual Target Attack (NTA), the first gradient-based attack that relies on a non-textual constrained objective to maximize the unsafety probability of the LLM output, without enforcing any response patterns. For tractable optimization, we further decompose this objective into two constrained sub-objectives, which can be approximated by two differentiable unconstrained losses, to iteratively optimize the response and the adversarial prompt in the neighborhood of the original prompt, with a theoretical analysis to validate the decomposition. In contrast to existing attacks, NTA first realizes gradient-based prompt optimization on a non-textual target and significantly expands the attack space, enabling more flexible and efficient exploration of LLM vulnerabilities. Extensive evaluations show that \textsc{NTA} achieves an average attack success rate of 96.8% against recent safety-aligned LLMs with only 100 optimization iterations on AdvBench, outperforming state-of-the-art gradient-based attacks by over 40%.

Emerging Large Reasoning Models (LRMs) consistently excel in mathematical and reasoning tasks, showcasing remarkable capabilities. However, the enhancement of reasoning abilities and the exposure of internal reasoning processes introduce new safety vulnerabilities. A critical question arises: when reasoning becomes intertwined with harmfulness, will LRMs become more vulnerable to jailbreaks in reasoning mode? To investigate this, we introduce HauntAttack, a novel and general-purpose black-box adversarial attack framework that systematically embeds harmful instructions into reasoning questions. Specifically, we modify key reasoning conditions in existing questions with harmful instructions, thereby constructing a reasoning pathway that guides the model step by step toward unsafe outputs. We evaluate HauntAttack on 11 LRMs and observe an average attack success rate of over 70%, achieving up to 13 percentage points of absolute improvement over the strongest prior baseline. Our further analysis reveals that even advanced safety-aligned models remain highly susceptible to reasoning-based attacks, offering insights into the urgent challenge of balancing reasoning capability and safety in future model development.

Diffusion models excel at generating high-quality images but can memorize and reproduce harmful concepts when prompted. Although fine-tuning methods have been proposed to unlearn a target concept, they struggle to fully erase it while maintaining generation quality on other concepts, leaving models vulnerable to jailbreak attacks. Existing jailbreak methods demonstrate this vulnerability but offer limited insight into how unlearned models retain harmful concepts, limiting progress on effective defenses. In this work, we show that a coherent, interpretable, attack-accessible linear residual of the erased concept can be recovered in the token embedding space, and that both an attack and a defense follow from this structure. We introduce SubAttack, a novel jailbreaking attack that reads out this subspace by learning an orthogonal set of attack token embeddings, each being a linear combination of human-interpretable textual elements, revealing that unlearned models still retain the target concept through related textual components. Furthermore, our attack is also more powerful and transferable across text prompts, initial noises, and unlearned models than prior attacks. Conversely, projecting out the same subspace yields SubDefense, a lightweight plug-and-play defense mechanism that suppresses the residual concept in unlearned models. SubDefense provides stronger robustness than existing defenses while better preserving safe generation quality. Extensive experiments across multiple unlearning methods, concepts, and attack types demonstrate that our approach advances both understanding and mitigation of vulnerabilities in diffusion unlearning.