Black-Box Red Teaming of Agentic AI: A Taxonomy-Driven Framework for Automated Risk Discovery

Agentic AI systems powered by large language models (LLMs) are rapidly evolving into autonomous decision-making systems, exposing attack vectors beyond those of traditional LLM vulnerabilities. Existing security evaluations are often tied to specific implementations or domains, limiting unified comparison across heterogeneous systems. To address this gap, we introduce RIFT-Bench, a representation-driven methodology for dynamic red-teaming that enables unified evaluations across diverse agentic architectures. Building on a novel hierarchical representation, RIFT-Bench operates in two automated phases: Discovery, which extracts system structure, and Scanning, which executes adaptive adversarial attacks. It directly evaluates the examined system using 105 adaptive adversarial probes spanning diverse attack vectors and objectives. We demonstrate the effectiveness of the proposed evaluation pipeline across 45 agentic systems spanning a diverse range of implementations, showing that the approach generalizes effectively to heterogeneous agentic architectures. Beyond systems and attacks, RIFT-Bench also supports direct evaluation of mitigation strategies. These key capabilities make RIFT-Bench a scalable foundation for security evaluation of agentic AI systems in practice. Infrastructure code and benchmark artifacts are available at https://tinyurl.com/RIFTBench.

AI agents are increasingly deployed across diverse domains to automate complex workflows through long-horizon and high-stakes action executions. Due to their high capability and flexibility, such agents raise significant security and safety concerns. A growing number of real-world incidents have shown that adversaries can easily manipulate agents into performing harmful actions, such as leaking API keys, deleting user data, or initiating unauthorized transactions. Evaluating agent security is inherently challenging, as agents operate in dynamic, untrusted environments involving external tools, heterogeneous data sources, and frequent user interactions. However, realistic, controllable, and reproducible environments for large-scale risk assessment remain largely underexplored. To address this gap, we introduce the DecodingTrust-Agent Platform (DTap), the first controllable and interactive red-teaming platform for AI agents, spanning 14 real-world domains and over 50 simulation environments that replicate widely used systems such as Google Workspace, Paypal, and Slack. To scale the risk assessment of agents in DTap, we further propose DTap-Red, the first autonomous red-teaming agent that systematically explores diverse injection vectors (e.g., prompt, tool, skill, environment, combinations) and autonomously discovers effective attack strategies tailored to varying malicious goals. Using DTap-Red, we curate DTap-Bench, a large-scale red-teaming dataset comprising high-quality instances across domains, each paired with a verifiable judge to automatically validate attack outcomes. Through DTap, we conduct large-scale evaluations of popular AI agents built on various backbone models, spanning security policies, risk categories, and attack strategies, revealing systematic vulnerability patterns and providing valuable insights for developing secure next-generation agents.

Production LLM agents such as Claude Code and Codex operate over untrusted content, files, commands, and workspace state, making safety failures directly actionable. Red-teaming must therefore keep pace with evolving models and tools. Existing approaches mainly optimize attack success and preserve artifacts such as benchmarks, payloads, or attack programs, which record where attacks succeed but not the enabling conditions behind unsafe agent behavior. We study automated red-teaming for production LLM agents using one agentic research environment to discover reusable vulnerability knowledge about another. We present AHA, a falsifiable discovery loop that proposes a vulnerability hypothesis, constructs a falsifier, instantiates a valid attack, executes it in a sandboxed harness, reflects on the trajectory, and promotes confirmed findings into a Vulnerability Concept Graph (VCG). Each concept links an attacker-facing surface to an unsafe trajectory through a claim, enabling condition, falsifier, transfer prediction, and supporting evidence. Across Claude Code and Codex on three scenarios covering direct and indirect attacks, the discovered concepts reveal a reusable vulnerability core across models and agents. A frozen VCG requires no further search and outperforms the strongest frozen discovery baseline by 14.2 percentage points under the same single-shot protocol, while transferring across scenarios and attack channels. The resulting VCG provides an auditable artifact for production safety teams to inspect vulnerabilities, validate patches, and accumulate reusable safety knowledge. Our code is available at https://github.com/henrymao2004/Auto-research-red-teaming-in-sleep.