Trusted Execution Environments (TEEs) (e.g., Intel SGX and ArmTrustZone) aim to protect sensitive computation from a compromised operating system, yet real deployments remain vulnerable to microarchitectural leakage, side-channel attacks, and fault injection. In parallel, security teams increasingly rely on Large Language Model (LLM) assistants as security advisors for TEE architecture review, mitigation planning, and vulnerability triage. This creates a socio-technical risk surface: assistants may hallucinate TEE mechanisms, overclaim guarantees (e.g., what attestation does and does not establish), or behave unsafely under adversarial prompting. We present a red-teaming study of two prevalently deployed LLM assistants in the role of TEE security advisors: ChatGPT-5.2 and Claude Opus-4.6, focusing on the inherent limitations and transferability of prompt-induced failures across LLMs. We introduce TEE-RedBench, a TEE-grounded evaluation methodology comprising (i) a TEE-specific threat model for LLM-mediated security work, (ii) a structured prompt suite spanning SGX and TrustZone architecture, attestation and key management, threat modeling, and non-operational mitigation guidance, along with policy-bound misuse probes, and (iii) an annotation rubric that jointly measures technical correctness, groundedness, uncertainty calibration, refusal quality, and safe helpfulness. We find that some failures are not purely idiosyncratic, transferring up to 12.02% across LLM assistants, and we connect these outcomes to secure architecture by outlining an "LLM-in-the-loop" evaluation pipeline: policy gating, retrieval grounding, structured templates, and lightweight verification checks that, when combined, reduce failures by 80.62%.

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 AttackPilot, 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.