Inference attacks have been widely studied and offer a systematic risk assessment of ML services; however, their implementation and the attack parameters for optimal estimation are challenging for non-experts. The emergence of advanced large language models presents a promising yet largely unexplored opportunity to develop autonomous agents as inference attack experts, helping address this challenge. In this paper, we propose InferPilot, an autonomous agent capable of independently conducting inference attacks without human intervention. We evaluate it on 20 target services. The evaluation shows that our agent, using GPT-4o, achieves a 100.0% task completion rate and near-expert attack performance, with an average token cost of only 0.627 per run. The agent can also be powered by many other representative LLMs and can adaptively optimize its strategy under service constraints. We further perform trace analysis, demonstrating that design choices, such as a multi-agent framework and task-specific action spaces, effectively mitigate errors such as bad plans, inability to follow instructions, task context loss, and hallucinations. We anticipate that such agents could empower non-expert ML service providers, auditors, or regulators to systematically assess the risks of ML services without requiring deep domain expertise.

With the rapid adoption of large language models (LLMs), conversational AI agents have become widely deployed across real-world applications. To enhance safety, these agents are often equipped with guardrails that moderate harmful content. Identifying the guardrails in an agent thus becomes critical for adversaries to understand the system and design guard-specific attacks. In this work, we introduce AP-Test, a novel approach that leverages guard-specific adversarial prompts to detect the identity of guardrails deployed in black-box AI agents. Our method addresses key challenges in this task, including the influence of safety-aligned LLMs and other guardrails, as well as a lack of principled decision-making strategies. AP-Test employs two complementary testing strategies, input and output guard tests, and a new metric, match score, to enable robust identification. Experiments across diverse agents and four open-source guardrails demonstrate that AP-Test achieves perfect classification accuracy in multiple scenarios. Ablation studies further highlight the necessity of our proposed components. Our findings reveal a practical path toward guardrail identification in real-world AI systems.

Large language models (LLMs) remain vulnerable to multi-turn jailbreaking attacks that exploit conversational context to bypass safety constraints gradually. These attacks target different harm categories through distinct conversational approaches. Existing multi-turn methods often rely on heuristic or ad hoc exploration strategies, providing limited insight into underlying model weaknesses. The relationship between conversation patterns and model vulnerabilities across harm categories remains poorly understood. We propose Pattern Enhanced Chain of Attack (PE-CoA), a framework of five conversation patterns to construct multi-turn jailbreaks through natural dialogue. Evaluating PE-CoA on twelve LLMs spanning ten harm categories, we achieve state-of-the-art performance, uncovering pattern-specific vulnerabilities and LLM behavioral characteristics: models exhibit distinct weakness profiles, defense to one pattern does not generalize to others, and model families share similar failure modes. These findings highlight limitations of safety training and indicate the need for pattern-aware defenses. Code available on: https://github.com/Ragib-Amin-Nihal/PE-CoA