Rouxii: Exploiting Honeypots with Deception-Aware AI Pentesters

Honeypots are designed to deceive attackers, and recent work shows they can also derail autonomous LLM-based pentesters. These evaluations, however, largely consider attackers unaware of the deception they face. We study the opposite setting: an autonomous attacker explicitly equipped to recognize and act on honeypot fingerprints. We introduce Rouxii, an AI-driven penetration-testing framework that integrates counter-deception into reconnaissance and pivots from honeypot detection to exploitation. We evaluate matched vanilla and anti-deception Rouxii configurations across three reasoning models and eleven network setups over twelve cycles (1,544 attack reports). Between the matched cohorts, which differ only in the prompt, counter-deception raises correct honeypot identification from 19% to 97%, an effect strongest on OT services (11% to 97%), while false alarms on the real service stay at 0.7%. Deception-unaware baselines (PentestGPT, HackingBuddy) fail similarly, indicating the effect is not specific to our framework. Detection, moreover, is not the endpoint: through a white-box analysis of the honeypots themselves we show that a detected trap can be turned against its operator, demonstrating a denial-of-service that disables Conpot without tripping its liveness monitoring, and a corruption of the intelligence a GasPot instance reports. These findings show that deception effectiveness depends strongly on attacker knowledge, and that evaluations of honeypot resilience against AI attackers must account for adversaries that actively reason about and exploit the deception layer.