Large language model agents automate web penetration testing through observation-action loops, enabling defenders to influence decisions with deceptive decoy observations. Advanced agents can recognize and bypass static decoys, then refocus on real targets. We propose AgentSnare, a trajectory-adaptive deception system that expands a decoy environment alongside exploration. For online deployment, ShadowOS combines an LLM-driven decoy constructor with a virtual kernel. Conditioned on exploration, it generates decoy artifacts that the kernel materializes and handles consistently across interactions, sustaining long-horizon exploration. Because deploying a powerful LLM for decoy construction is costly and slow, we train a small LLM using an offline adversarial interaction-simulation framework. It synthesizes multi-round trajectories by generating candidates and retaining those that sustain simulated interactions. Across 15 CVE-Bench web applications and four attacker models, AgentSnare absorbs 49.9% of tool calls to delay attacks, retains 57.2% of post-entry actions in the decoy to divert trajectories, and grounds 89.5% of completion reports in decoy evidence to defuse threats; across 60 attacker-CVE pairs, no real target is exploited at pass@3.

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