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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. less

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. less

Prompt injection attacks pose serious security risks across a wide range of real-world applications. While receiving increasing attention, the community faces a critical gap: the lack of a unified platform for prompt injection evaluation. This makes it challenging to reliably compare defenses, understand their true robustness under diverse attacks, or assess how well they generalize across tasks and benchmarks. For instance, many defenses initially reported as effective were later found to exhibit limited robustness on diverse datasets and attacks. To bridge this gap, we introduce PIArena, a unified and extensible platform for prompt injection evaluation that enables users to easily integrate state-of-the-art attacks and defenses and evaluate them across a variety of existing and new benchmarks. We also design a dynamic strategy-based attack that adaptively optimizes injected prompts based on defense feedback. Through comprehensive evaluation using PIArena, we uncover critical limitations of state-of-the-art defenses: limited generalizability across tasks, vulnerability to adaptive attacks, and fundamental challenges when an injected task aligns with the target task. The code and datasets are available at https://github.com/sleeepeer/PIArena. less

As large language models (LLMs) evolve from static chatbots into autonomous agents, the primary vulnerability surface shifts from final outputs to intermediate execution traces. While safety guardrails are well-benchmarked for natural language responses, their efficacy remains largely unexplored within multi-step tool-use trajectories. To address this gap, we introduce TraceSafe-Bench, the first comprehensive benchmark specifically designed to assess mid-trajectory safety. It encompasses 12 risk categories, ranging from security threats (e.g., prompt injection, privacy leaks) to operational failures (e.g., hallucinations, interface inconsistencies), featuring over 1,000 unique execution instances. Our evaluation of 13 LLM-as-a-guard models and 7 specialized guardrails yields three critical findings: 1) Structural Bottleneck: Guardrail efficacy is driven more by structural data competence (e.g., JSON parsing) than semantic safety alignment. Performance correlates strongly with structured-to-text benchmarks ($ρ=0.79$) but shows near-zero correlation with standard jailbreak robustness. 2) Architecture over Scale: Model architecture influences risk detection performance more significantly than model size, with general-purpose LLMs consistently outperforming specialized safety guardrails in trajectory analysis. 3) Temporal Stability: Accuracy remains resilient across extended trajectories. Increased execution steps allow models to pivot from static tool definitions to dynamic execution behaviors, actually improving risk detection performance in later stages. Our findings suggest that securing agentic workflows requires jointly optimizing for structural reasoning and safety alignment to effectively mitigate mid-trajectory risks. less

Accurately determining whether a jailbreak attempt has succeeded is a fundamental yet unresolved challenge. Existing evaluation methods rely on misaligned proxy indicators or naive holistic judgments. They frequently misinterpret model responses, leading to inconsistent and subjective assessments that misalign with human perception. To address this gap, we introduce JADES (Jailbreak Assessment via Decompositional Scoring), a universal jailbreak evaluation framework. Its key mechanism is to automatically decompose an input harmful question into a set of weighted sub-questions, score each sub-answer, and weight-aggregate the sub-scores into a final decision. JADES also incorporates an optional fact-checking module to strengthen the detection of hallucinations in jailbreak responses. We validate JADES on JailbreakQR, a newly introduced benchmark proposed in this work, consisting of 400 pairs of jailbreak prompts and responses, each meticulously annotated by humans. In a binary setting (success/failure), JADES achieves 98.5% agreement with human evaluators, outperforming strong baselines by over 9%. Re-evaluating five popular attacks on four LLMs reveals substantial overestimation (e.g., LAA's attack success rate on GPT-3.5-Turbo drops from 93% to 69%). Our results show that JADES could deliver accurate, consistent, and interpretable evaluations, providing a reliable basis for measuring future jailbreak attacks. less

Large Language Models (LLMs) have transformed human-machine interaction since ChatGPT's 2022 debut, with Retrieval-Augmented Generation (RAG) emerging as a key framework that enhances LLM outputs by integrating external knowledge. However, RAG's reliance on ingesting external documents introduces new vulnerabilities. This paper exposes a critical security gap at the data loading stage, where malicious actors can stealthily corrupt RAG pipelines by exploiting document ingestion. We propose a taxonomy of 9 knowledge-based poisoning attacks and introduce two novel threat vectors -- Content Obfuscation and Content Injection -- targeting common formats (DOCX, HTML, PDF). Using an automated toolkit implementing 19 stealthy injection techniques, we test five popular data loaders, finding a 74.4% attack success rate across 357 scenarios. We further validate these threats on six end-to-end RAG systems -- including white-box pipelines and black-box services like NotebookLM and OpenAI Assistants -- demonstrating high success rates and critical vulnerabilities that bypass filters and silently compromise output integrity. Our results emphasize the urgent need to secure the document ingestion process in RAG systems against covert content manipulations. less

Indirect Prompt Injection attacks exploit the inherent limitation of Large Language Models (LLMs) to distinguish between instructions and data in their inputs. Despite numerous defense proposals, the systematic evaluation against adaptive adversaries remains limited, even when successful attacks can have wide security and privacy implications, and many real-world LLM-based applications remain vulnerable. We present the results of LLMail-Inject, a public challenge simulating a realistic scenario in which participants adaptively attempted to inject malicious instructions into emails in order to trigger unauthorized tool calls in an LLM-based email assistant. The challenge spanned multiple defense strategies, LLM architectures, and retrieval configurations, resulting in a dataset of 208,095 unique attack submissions from 839 participants. We release the challenge code, the full dataset of submissions, and our analysis demonstrating how this data can provide new insights into the instruction-data separation problem. We hope this will serve as a foundation for future research towards practical structural solutions to prompt injection. less

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