Language Model Evasion Attacks

The growth of agentic AI has drawn significant attention to function calling Large Language Models (LLMs), which are designed to extend the capabilities of AI-powered system by invoking external functions. Injection and jailbreaking attacks have been extensively explored to showcase the vulnerabilities of LLMs to user prompt manipulation. The expanded capabilities of agentic models introduce further vulnerabilities via their function calling interface. Recent work in LLM security showed that function calling can be abused, leading to data tampering and theft, causing disruptive behavior such as endless loops, or causing LLMs to produce harmful content in the style of jailbreaking attacks. This paper introduces a novel function hijacking attack (FHA) that manipulates the tool selection process of agentic models to force the invocation of an attacker-chosen function. While existing attacks focus on semantic preference of the model for function-calling tasks, we show that FHA is largely agnostic to the context semantics and remains effective across domains and function sets. We demonstrate that FHA generalizes to unseen queries and payload perturbations under a fixed target model, reaching 62.5% to 81.9% ASR on held-out queries across 4 function-calling LLMs (instructed and reasoning models), evaluated on the Berkeley Function Calling Leaderboard (BFCL). We further evaluate the cross-model transferability of FHA, showing that FHA can be transferred to other model sizes and families (11.2-27.6% ASR). Our findings further demonstrate the need for strong guardrails and modules for agentic systems.

Current benchmarks for evaluating large language models (LLMs) in social media moderation completely overlook a serious threat: covert advertisements, which disguise themselves as regular posts to deceive and mislead consumers into making purchases, leading to significant ethical and legal concerns. In this paper, we present the CHASM, a first-of-its-kind dataset designed to evaluate the capability of Multimodal Large Language Models (MLLMs) in detecting covert advertisements on social media. CHASM is a high-quality, anonymized, manually curated dataset consisting of 4,992 instances, based on real-world scenarios from the Chinese social media platform Rednote. The dataset was collected and annotated under strict privacy protection and quality control protocols. It includes many product experience sharing posts that closely resemble covert advertisements, making the dataset particularly challenging.The results show that under both zero-shot and in-context learning settings, none of the current MLLMs are sufficiently reliable for detecting covert advertisements.Our further experiments revealed that fine-tuning open-source MLLMs on our dataset yielded noticeable performance gains. However, significant challenges persist, such as detecting subtle cues in comments and differences in visual and textual structures.We provide in-depth error analysis and outline future research directions. We hope our study can serve as a call for the research community and platform moderators to develop more precise defenses against this emerging threat.

Cross-site scripting (XSS) remains a persistent web security vulnerability, especially because obfuscation can change the surface form of a malicious payload while preserving its behavior. These transformations make it difficult for traditional and machine learning-based detection systems to reliably identify attacks. Existing approaches for generating obfuscated payloads often emphasize syntactic diversity, but they do not always ensure that the generated samples remain behaviorally valid. This paper presents a structured pipeline for generating and evaluating obfuscated XSS payloads using large language models (LLMs). The pipeline combines deterministic transformation techniques with LLM-based generation and uses a browser- based runtime evaluation procedure to compare payload behavior in a controlled execution environment. This allows generated samples to be assessed through observable runtime behavior rather than syntactic similarity alone. In the evaluation, an untuned baseline language model achieves a runtime behavior match rate of 0.15, while fine-tuning on behavior-preserving source-target obfuscation pairs improves the match rate to 0.22. Although this represents a measurable improvement, the results show that current LLMs still struggle to generate obfuscations that preserve observed runtime behavior. A downstream classifier evaluation further shows that adding generated payloads does not improve detection performance in this setting, although behavior- filtered generated samples can be incorporated without materially degrading performance. Overall, the study demonstrates both the promise and the limits of applying generative models to adversarial security data generation and emphasizes the importance of runtime behavior checks in improving the quality of generated data for downstream detection systems.

Large Language Model (LLM) agents are increasingly proposed for autonomous cybersecurity tasks, but their capabilities in realistic offensive settings remain poorly understood. We present DeepRed, an open-source benchmark for evaluating LLM-based agents on realistic Capture The Flag (CTF) challenges in isolated virtualized environments. DeepRed places an agent in a Kali attacker environment with terminal tools and optional web search, connected over a private network to a target challenge, and records full execution traces for analysis. To move beyond binary solved/unsolved outcomes, we introduce a partial-credit scoring method based on challenge-specific checkpoints derived from public writeups, together with an automated summarise-then-judge labelling pipeline for assigning checkpoint completion from logs. Using DeepRed, we benchmark ten commercially accessible LLMs on ten VM-based CTF challenges spanning different challenge categories. The results indicate that current agents remain limited: the best model achieves only 35% average checkpoint completion, performing strongest on common challenge types and weakest on tasks requiring non-standard discovery and longer-horizon adaptation.

While Large Language Models (LLMs) are widely used, they remain susceptible to jailbreak prompts that can elicit harmful or inappropriate responses. This paper introduces STAR-Teaming, a novel black-box framework for automated red teaming that effectively generates such prompts. STAR-Teaming integrates a Multi-Agent System (MAS) with a Strategy-Response Multiplex Network and employs network-driven optimization to sample effective attack strategies. This network-based approach recasts the intractable high-dimensional embedding space into a tractable structure, yielding two key advantages: it enhances the interpretability of the LLM's strategic vulnerabilities, and it streamlines the search for effective strategies by organizing the search space into semantic communities, thereby preventing redundant exploration. Empirical results demonstrate that STAR-Teaming significantly surpasses existing methods, achieving a higher attack success rate (ASR) at a lower computational cost. Extensive experiments validate the effectiveness and explainability of the Multiplex Network. The code is available at https://github.com/selectstar-ai/STAR-Teaming-paper.

Large Language Models (LLMs) are increasingly used in education, yet their default helpfulness often conflicts with pedagogical principles. Prior work evaluates pedagogical quality via answer leakage-the disclosure of complete solutions instead of scaffolding-but typically assumes well-intentioned learners, leaving tutor robustness under student misuse largely unexplored. In this paper, we study scenarios where students behave adversarially and aim to obtain the correct answer from the tutor. We evaluate a broad set of LLM-based tutor models, including different model families, pedagogically aligned models, and a multi-agent design, under a range of adversarial student attacks. We adapt six groups of adversarial and persuasive techniques to the educational setting and use them to probe how likely a tutor is to reveal the final answer. We evaluate answer leakage robustness using different types of in-context adversarial student agents, finding that they often fail to carry out effective attacks. We therefore introduce an adversarial student agent that we fine-tune to jailbreak LLM-based tutors, which we propose as the core of a standardized benchmark for evaluating tutor robustness. Finally, we present simple but effective defense strategies that reduce answer leakage and strengthen the robustness of LLM-based tutors in adversarial scenarios.

We present, to our knowledge, the most comprehensive cross-model evaluation of LLM agents on offensive cybersecurity tasks, benchmarking 10 frontier models from 7 providers on all 200 challenges of the NYU CTF Bench. Building on the D-CIPHER multi-agent framework, we extend it with multi-provider backend support, a custom Kali Linux environment with over 100 pre-installed penetration testing tools, and runtime tool-discovery agents. Through a controlled factorial study, we find that the Kali Linux environment yields a +9.5 percentage-point improvement over Ubuntu, while auto-prompting and category-specific tips often degrade performance in well-equipped environments. Among models, Claude 4.5 Opus achieves the highest solve rate (59%), followed by Gemini 3 Pro (52%), with Gemini 3 Flash offering the best cost-efficiency at $0.05 per solve. Asymmetric planner/executor model assignments provide no meaningful benefit while coherent same-model configurations consistently outperform mixed-tier pairings. Our results indicate that environment tooling and model selection emerge as the strongest drivers of performance, whereas prompt engineering interventions show diminishing or negative returns in well-equipped environments. Reported performance reflects both model reasoning ability and compatibility with agent tooling and API integration.

When model developers or users fine-tune an LLM, this can induce behaviors that are unexpected, deliberately harmful, or hard to detect. It would be far easier to audit LLMs if they could simply describe their behaviors in natural language. Here, we study a scalable approach to rapidly identify learned behaviors of many LLMs derived from a shared base LLM. Given a model $M$, our method works by finetuning models $M_i$ from $M$ with implanted behaviors $b_i$; the $(M_i, b_i)$ pairs serve as labeled training data. We then train an introspection adapter (IA): a single LoRA adapter jointly trained across the finetunes $M_i$ to cause them to verbalize their implanted behaviors. We find that this IA induces self-description of learned behaviors even in finetunes of $M$ that were trained in very different ways from the $M_i$. For example, IAs generalize to AuditBench, achieving state-of-the-art at identifying explicitly hidden concerning behaviors. IAs can also be used to detect encrypted finetuning API attacks. They scale favorably with model size and training data diversity. Overall, our results suggest that IAs are a scalable, effective, and practically useful approach to auditing fine-tuned LLMs.

Most LLM safety work studies single-agent models, but many real applications rely on multiple interacting agents. In these systems, prompt segmentation and inter-agent routing create attack surfaces that single-agent evaluations miss. We study \emph{conjunctive prompt attacks}, where a trigger key in the user query and a hidden adversarial template in one compromised remote agent each appear benign alone but activate harmful behavior when routing brings them together. We consider an attacker who changes neither model weights nor the client agent and instead controls only trigger placement and template insertion. Across star, chain, and DAG topologies, routing-aware optimization substantially increases attack success over non-optimized baselines while keeping false activations low. Existing defenses, including PromptGuard, Llama-Guard variants, and system-level controls such as tool restrictions, do not reliably stop the attack because no single component appears malicious in isolation. These results expose a structural vulnerability in agentic LLM pipelines and motivate defenses that reason over routing and cross-agent composition. Code is available at https://github.com/UCF-ML-Research/ConjunctiveAgents.

Cost-aware routing dynamically dispatches user queries to models of varying capability to balance performance and inference cost. However, the routing strategy introduces a new security concern that adversaries may manipulate the router to consistently select expensive high-capability models. Existing routing attacks depend on either white-box access or heuristic prompts, rendering them ineffective in real-world black-box scenarios. In this work, we propose R$^2$A, which aims to mislead black-box LLM routers to expensive models via adversarial suffix optimization. Specifically, R$^2$A deploys a hybrid ensemble surrogate router to mimic the black-box router. A suffix optimization algorithm is further adapted for the ensemble-based surrogate. Extensive experiments on multiple open-source and commercial routing systems demonstrate that {R$^2$A} significantly increases the routing rate to expensive models on queries of different distributions. Code and examples: https://github.com/thcxiker/R2A-Attack.

While prior red-teaming efforts have focused on eliciting harmful text outputs from large language models (LLMs), such approaches fail to capture agent-specific vulnerabilities that emerge through multi-step tool execution, particularly in rapidly growing ecosystems such as the Model Context Protocol (MCP). To address this gap, we propose a trajectory-aware evolutionary search method, T-MAP, which leverages execution trajectories to guide the discovery of adversarial prompts. Our approach enables the automatic generation of attacks that not only bypass safety guardrails but also reliably realize harmful objectives through actual tool interactions. Empirical evaluations across diverse MCP environments demonstrate that T-MAP substantially outperforms baselines in attack realization rate (ARR) and remains effective against frontier models, including GPT-5.2, Gemini-3-Pro, Qwen3.5, and GLM-5, thereby revealing previously underexplored vulnerabilities in autonomous LLM agents. Code is available at https://github.com/pwnhyo/T-MAP.

LLMs see the world as a single stream of text, partitioned into roles like <user> or <tool>. We trace prompt injection to role confusion: models perceive the source of text from how it sounds, not its labeled role. A command hidden in a webpage hijacks an agent simply because it sounds like <user> text, despite its <tool> label. We design role probes to measure how LLMs internally perceive "who is speaking," and find that injected text occupies the same representational space as the trusted role it imitates. We demonstrate this with CoT Forgery, a zero-shot attack that injects fabricated reasoning into user prompts and tool outputs. Models mistake the forgery for their own thoughts, yielding 60% attack success against frontier models with near-zero baselines. Strikingly, the degree of role confusion predicts attack success before a single token is generated. This mechanism generalizes beyond CoT Forgery to standard agent prompt injections, revealing prompt injection as a measurable consequence of role perception. To the model, sounding like a role is indistinguishable from being one. Project page and writeup: https://role-confusion.github.io

Semantic caching has emerged as a pivotal technique for scaling LLM applications, widely adopted by major providers including AWS and Microsoft. By utilizing semantic embedding vectors as cache keys, this mechanism effectively minimizes latency and redundant computation for semantically similar queries. In this work, we conceptualize semantic cache keys as a form of fuzzy hashes. We demonstrate that the locality required to maximize cache hit rates fundamentally conflicts with the cryptographic avalanche effect necessary for collision resistance. Our conceptual analysis formalizes this inherent trade-off between performance (locality) and security (collision resilience), revealing that semantic caching is naturally vulnerable to key collision attacks. While prior research has focused on side-channel and privacy risks, we present the first systematic study of integrity risks arising from cache collisions. We introduce CacheAttack, an automated framework for launching black-box collision attacks. We evaluate CacheAttack in security-critical tasks and agentic workflows. It achieves a hit rate of 86% in LLM response hijacking and can induce malicious behaviors in LLM agent, while preserving strong transferability across different embedding models. A case study on a financial agent further illustrates the real-world impact of these vulnerabilities. Finally, we discuss mitigation strategies.

Modern LLMs are increasingly accessed via black-box APIs, requiring users to transmit sensitive prompts, outputs, and fine-tuning data to external providers, creating a critical privacy risk at the API boundary. We introduce AlienLM, a deployable API-only \cradd{exposure-reduction layer that reduces plaintext exposure} by translating text into an Alien Language via a vocabulary-scale bijection, enabling lossless recovery on the client side. Using only standard fine-tuning APIs, Alien Adaptation Training (AAT) adapts target models to operate directly on alienized inputs. Across four LLM backbones and seven benchmarks, AlienLM retains over 81% of plaintext-oracle performance on average, substantially outperforming random-bijection and character-level baselines. Under adversaries with access to model weights, corpus statistics, and learning-based inverse translation, recovery attacks reconstruct fewer than 0.22% of alienized tokens. Our results demonstrate a practical pathway for \cradd{privacy-aware} LLM deployment under API-only access, substantially reducing plaintext exposure while maintaining task performance. Code and data are available at https://github.com/KimJaehee0725/AlienLM.

Autonomous code agents built on large language models are reshaping software and AI development through tool use, long-horizon reasoning, and self-directed interaction. However, this autonomy introduces a previously unrecognized security risk: agentic interaction fundamentally expands the LLM attack surface, enabling systematic probing and recovery of hidden system prompts that guide model behavior. We identify system prompt extraction as an emergent vulnerability intrinsic to code agents and present \textbf{\textsc{JustAsk}}, a self-evolving framework that autonomously discovers effective extraction strategies through interaction alone. Unlike prior prompt-engineering or dataset-based attacks, \textsc{JustAsk} requires no handcrafted prompts, labeled supervision, or privileged access beyond standard user interaction. It formulates extraction as an online exploration problem, using Upper Confidence Bound-based strategy selection and a hierarchical skill space spanning atomic probes and high-level orchestration. These skills exploit imperfect system-instruction generalization and inherent tensions between helpfulness and safety. Evaluated on \textbf{41} black-box commercial models across multiple providers, \textsc{JustAsk} consistently achieves full or near-complete system prompt recovery, revealing recurring design- and architecture-level vulnerabilities. Our results expose system prompts as a critical yet largely unprotected attack surface in modern agent systems.

State space models (SSMs) like Mamba offer efficient alternatives to Transformer-based language models, with linear time complexity. Yet, their adversarial robustness remains critically unexplored. This paper studies the phenomenon whereby specific short input phrases induce a partial amnesia effect in such models, by irreversibly overwriting information in their hidden states, referred to as a Hidden State Poisoning Attack (HiSPA). Our benchmark RoBench-25 allows evaluating a model's information retrieval capabilities when subject to HiSPAs, and confirms the vulnerability of SSMs against such attacks. Even the recent Jamba-1.7-Mini SSM--Transformer (a 52B hybrid model) collapses on RoBench-25 under some HiSPA triggers, whereas pure Transformers do not. We also observe that HiSPA triggers significantly weaken the Jamba model on the popular Open-Prompt-Injections benchmark, unlike pure Transformers. We further show that the theoretical and empirical findings extend to Mamba-2, and also analyse a Mamba-2-based hybrid (Nemotron-3-Nano). Finally, our interpretability study reveals patterns in Mamba's hidden layers during HiSPAs that could be used to build a HiSPA mitigation system. The full code and data to reproduce the experiments can be found at https://github.com/TortueSagace/hispa.

When answering user queries, LLMs often retrieve knowledge from external sources stored in retrieval-augmented generation (RAG) databases. These are often populated from unvetted sources, e.g. the open web, and can contain maliciously crafted data. This paper studies attacks that can manipulate the context retrieved by LLMs from such RAG databases. Prior work on such context manipulation primarily injects false or toxic content, which can often be detected by fact-checking or linguistic analysis. A more subtle threat, which we call epistemic bias injection (EBI), is where adversaries inject factually correct yet epistemically biased passages that systematically favor one side of an open-ended issue. Although linguistically coherent and truthful, such adversarial passages effectively crowd out alternative viewpoints during retrieval from the RAG and push LLM outputs towards an attack-desired stance. As a core contribution, we propose a novel characterization of the problem: We give a geometric metric that quantifies stance polarity and epistemic bias. This metric can be computed directly on embeddings of text passages. Leveraging it, we construct EBI attacks and develop a lightweight prototype defense called BiasDef for them. We evaluate them both on a comprehensive benchmark constructed from public question answering datasets. Our results show that: (1) the proposed attack induces significant stance polarity shifts, effectively evading existing retrieval-based sanitization defenses, and (2) BiasDef substantially reduces adversarial retrieval and epistemic bias in LLM's answers. Overall, this demonstrates the new threat as well as the ease of employing epistemic bias metrics for filtering in RAG-enabled LLMs.

Large Language Model (LLM) agents are powering a growing share of interactive web applications, yet remain vulnerable to misuse and harm. Prior jailbreak research has largely focused on single-turn prompts, whereas real harassment often unfolds over multi-turn interactions. In this work, we present the Online Harassment Agentic Benchmark consisting of: (i) a synthetic multi-turn harassment conversation dataset, (ii) a multi-agent (e.g., harasser, victim) simulation informed by repeated game theory, (iii) three jailbreak methods attacking agents across memory, planning, and fine-tuning, and (iv) a mixed-methods evaluation framework. We utilize two prominent LLMs, LLaMA-3.1-8B-Instruct (open-source) and Gemini-2.0-flash (closed-source). Our results show that jailbreak tuning makes harassment nearly guaranteed with an attack success rate of 95.78--96.89% vs. 57.25--64.19% without tuning in Llama, and 99.33% vs. 98.46% without tuning in Gemini, while sharply reducing refusal rate to 1-2% in both models. The most prevalent toxic behaviors are Insult with 84.9--87.8% vs. 44.2--50.8% without tuning, and Flaming with 81.2--85.1% vs. 31.5--38.8% without tuning, indicating weaker guardrails compared to sensitive categories such as sexual or racial harassment. Qualitative evaluation further reveals that attacked agents reproduce human-like aggression profiles, such as Machiavellian/psychopathic patterns under planning, and narcissistic tendencies with memory. Counterintuitively, closed-source and open-source models exhibit distinct escalation trajectories across turns, with closed-source models showing significant vulnerability. Overall, our findings show that multi-turn and theory-grounded attacks not only succeed at high rates but also mimic human-like harassment dynamics, motivating the development of robust safety guardrails to ultimately keep online platforms safe and responsible.

The proliferation of Large Language Models (LLMs) has enabled a new class of psychologically grounded malicious comments, shifting fake news attacks from surface-level textual noise to deep cognitive and logical manipulation. This shift severely undermines existing detectors, which conventionally rely on static attack assumptions and fixed training distributions. To bridge this gap, we introduce CogniDir, an adaptive distributional learning framework that reformulates robust detection as a dynamic data mixture optimization problem for social media content safety. Grounded in cognitive psychology, we first formalize mechanism-specific cognitive adversarial paradigms to systematically expose deep-seated detector vulnerabilities. To address the vulnerability heterogeneity, CogniDir derives an information-theoretic score coupling empirical accuracy with probabilistic confidence, which is then mapped to adaptive sampling proportions through a Dirichlet-mean parameterization. This formulation enables smooth, feedback-driven reallocation of training exposure toward the most brittle attack mechanisms. Experimental results on three benchmarks demonstrate that CogniDir yields state-of-the-art robustness, improving F1 scores by up to 17.9% over competitive baselines under heterogeneous, AI-generated adversarial pressures.

Large Language Models (LLMs) for code generation (i.e., Code LLMs) have demonstrated impressive capabilities in AI-assisted software development and testing. However, recent studies have shown that these models are prone to generating vulnerable or even malicious code under adversarial settings. Existing red-teaming approaches rely on extensive human effort, limiting their scalability and practicality, and generally overlook the interactive nature of real-world AI-assisted programming, which often unfolds over multiple turns. To bridge these gaps, we present RedCoder, a red-teaming agent that engages victim models in multi-turn conversation to elicit vulnerable code. The pipeline to construct RedCoder begins with a multi-agent gaming process that simulates adversarial interactions, yielding a set of prototype conversations and an arsenal of reusable attack strategies. We then fine-tune an LLM on these prototype conversations to serve as the backbone of RedCoder. Once deployed, RedCoder autonomously engages Code LLMs in multi-turn conversations, dynamically retrieving relevant strategies from the arsenal to steer the dialogue toward vulnerability-inducing outputs. Experiments across multiple Code LLMs show that our approach outperforms prior single-turn and multi-turn red-team methods in inducing vulnerabilities in code generation, offering a scalable and effective tool for evaluating the security boundaries of modern code-generation systems.

Finetuning open-weight Large Language Models (LLMs) is standard practice for achieving task-specific performance improvements. Until now, finetuning has been regarded as a controlled and secure process in which training on benign datasets leads to predictable behaviors. In this paper, we demonstrate, for the first time, that an adversary can create compromised LLMs that are performant and benign, yet exhibit adversarial behaviors once finetuned by downstream users. To this end, we propose an attack, FAB (Finetuning-activated Adversarial Behaviors), which compromises an LLM via meta-learning techniques that simulate downstream finetuning, explicitly optimizing for the emergence of adversarial behaviors in the finetuned models. At the same time, the compromised LLM is regularized to retain general capabilities and to exhibit no adversarial behaviors prior to finetuning. As a result, when users finetune (e.g., instruction-tuning, distillation, DPO) the seemingly benign model on their own datasets, they unknowingly trigger its dormant adversarial behavior. We experimentally demonstrate the effectiveness of FAB across multiple LLMs and three commonly considered target behaviors: unsolicited advertising, jailbreakability, and over-refusal. We show that FAB-triggers are robust to various finetuning choices made by the user (e.g., dataset, number of steps, scheduler, post-training algorithm). Our findings challenge prevailing assumptions on the security of finetuning, revealing a critical attack vector.

Traditional white-box methods for creating adversarial perturbations against LLMs typically rely only on gradient computation from the targeted model, ignoring the internal mechanisms responsible for attack success or failure. Conversely, interpretability studies that analyze these internal mechanisms lack practical applications beyond runtime interventions. We bridge this gap by introducing a novel white-box approach that leverages mechanistic interpretability techniques to craft practical adversarial inputs. Specifically, we first identify acceptance subspaces - sets of feature vectors that do not trigger the model's refusal mechanisms - then use gradient-based optimization to reroute embeddings from refusal subspaces to acceptance subspaces, effectively achieving jailbreaks. This targeted approach significantly reduces computation cost, achieving attack success rates of 80-95% on state-of-the-art models including Gemma2, Llama3.2, and Qwen2.5 within minutes or even seconds, compared to existing techniques that often fail or require hours of computation. We believe this approach opens a new direction for both attack research and defense development. Furthermore, it showcases a practical application of mechanistic interpretability where other methods are less efficient, which highlights its utility. The code and generated datasets are available at https://github.com/Sckathach/subspace-rerouting.

The tremendous commercial potential of large language models (LLMs) has heightened concerns over their unauthorized use. To address this, we focus on the task of identifying the origin of black-box LLMs. We further propose PlugAE, an effective and efficient identification method that proactively leverages LLM-specific adversarial embeddings and allows users to customize copyright tokens on a targeted query set. Extensive experiments demonstrate that PlugAE outperforms both state-of-the-art model watermarking and fingerprinting methods in accuracy and robustness. We further analyze its stealthiness and reliability from three complementary perspectives and conduct ablation studies under various configurations, confirming its practicality for real-world misuse detection.

Red-teaming, or identifying prompts that elicit harmful responses, is a critical step in ensuring the safe and responsible deployment of large language models (LLMs). Developing effective protection against many modes of attack prompts requires discovering diverse attacks. Automated red-teaming typically uses reinforcement learning to fine-tune an attacker language model to generate prompts that elicit undesirable responses from a target LLM, as measured, for example, by an auxiliary toxicity classifier. We show that even with explicit regularization to favor novelty and diversity, existing approaches suffer from mode collapse or fail to generate effective attacks. As a flexible and probabilistically principled alternative, we propose to use GFlowNet fine-tuning, followed by a secondary smoothing phase, to train the attacker model to generate diverse and effective attack prompts. We find that the attacks generated by our method are effective against a wide range of target LLMs, both with and without safety tuning, and transfer well between target LLMs. Finally, we demonstrate that models safety-tuned using a dataset of red-teaming prompts generated by our method are robust to attacks from other RL-based red-teaming approaches.