LLM-powered autonomous agents are transforming the penetration testing space with dynamic, multi-step offensive security workflows that require minimal supervision by humans. These agents leverage sophisticated reasoning abilities and external security tools to independently carry out reconnaissance, identify vulnerabilities, devise exploitation plans, and perform post-exploitation operations. But the ability to have persistent memory, to take actions in the real world, and to do long-horizon reasoning raises qualitatively different security concerns than traditional chat-based LLM systems. Existing guardrail mechanisms for conversational AI may not be sufficient to secure autonomous AI pentesting agents accordingly. To address these issues, we carry out a comprehensive security analysis on autonomous AI-penetration testing agents. We systematically analyse representative agent architectures, characterise their trust boundaries and attack surfaces and propose a threat taxonomy that is aligned with the lifecycle and covers LLM lifecycle attacks, agent-architecture attacks and cross-cutting behavioural attacks. We analyse the limitations of existing guardrail mechanisms, identify key research gaps, and discuss future research directions for developing specialised, context-aware, and architecture-aware guardrails to secure next-generation AI-driven offensive security systems.

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