Mar 23, 2026

Beyond Prompt Injection: Offensive Security Tradecraft Exposes Architectural Blind Spot Classes in AI Control Monitors

John Kearney

AI control monitors that evaluate agent actions per-task struggle to detect attacks distributed across multiple individually-benign tasks. I applied offensive security tradecraft to ControlArena’s Opus 4.6 monitor using 22 attack transcripts across four categories. All 20 offensive transcripts evaded the default monitor. Against the full-trajectory monitor, TOCTOU attacks evaded at 100% and salami attacks at 80%, while living-off-the-land and text-only exfiltration were mostly caught. The difference is structural: TOCTOU and salami distribute the attack across separate evaluations that are each individually benign, so no single evaluation contains evidence of wrongdoing. Cross-model validation on Sonnet 4.5 confirmed this: content-based evasion disappeared entirely but structural evasion persisted. This structural/content-based distinction is the central finding: it separates attacks that yield to capability scaling from attacks that require architectural change, two fundamentally different problems. The report provides a taxonomy mapping offensive security patterns to monitor blind spot classes, a proof-of-concept aggregate monitor with cross-task state (caught 3/5 salami steps vs. 1/5 for per-task evaluation), ControlArena-compatible attack policies, and the first dataset bridging offensive security methodology with AI control red-teaming.

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Cite this work

@misc {

title={

(HckPrj) Beyond Prompt Injection: Offensive Security Tradecraft Exposes Architectural Blind Spot Classes in AI Control Monitors

},

author={

John Kearney

},

date={

3/23/26

},

organization={Apart Research},

note={Research submission to the research sprint hosted by Apart.},

howpublished={https://apartresearch.com}

}

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This work was done during one weekend by research workshop participants and does not represent the work of Apart Research.
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