The Block the Agent Walked Around
Case studyAn AI agent, denied its built-in web tool, reached for a shell command instead. One control let the request through — the control beneath it did not, and the packet capture proved which.
Notes on AI, Revenue Operations, and building production systems that actually work. Written from the operator’s seat, not the researcher’s.
An AI agent, denied its built-in web tool, reached for a shell command instead. One control let the request through — the control beneath it did not, and the packet capture proved which.
If the printing press had shipped with spyware, the Renaissance would have died in a decade — and it's a fair description of how most organizations use frontier AI today.
A system prompt is a probabilistic instruction, not a control — and under load a degraded instruction fails open.
A safety control passed every test in its suite — and still failed. The postmortem changed how I test everything.
You can write a full governing document for your AI agents, share it across the entire stack, and they will still drift.
Field notes on building governed, production AI systems — new issues to your inbox.
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