The Enterprise AI Brief | Issue 5
Inside This Issue
The Threat Room
BitBypass: Binary Word Substitution Defeats Multiple Guard Systems
BitBypass hides one sensitive word as a hyphen-separated bitstream, then uses system-prompt instructions to make the model decode and reinsert it. In testing across five frontier models, this approach substantially reduced refusal rates and bypassed multiple guard layers. All five tested models produced phishing content at rates between 68-92%. If your safety controls assume plain-language detection will catch malicious intent, this research deserves close attention.
The Operations Room
When Prompts Started Breaking Production
By early 2026, prompts were breaking production often enough that teams stopped treating them as configuration and started treating them like code: versioned, regression-tested, blocked in CI/CD when quality metrics slip. This is what happened when informal text became the functional interface defining system behavior, and why the teams that got ahead of it caught failures before their users did.
The Engineering Room
Structured Outputs Are Becoming the Default Contract for LLM Integrations
For two years, “return JSON” was a polite request followed by parsing code and retries when the model ignored you. Structured outputs move schema enforcement into the decoding layer, and the ecosystem is converging on this as the default contract. If your automations break when one field is missing, this shift changes what reliability means and where validation effort needs to sit.
The Governance Room
NIST’s Cyber AI Profile Draft: How CSF 2.0 Is Being Extended to AI Cybersecurity
NIST just tried to solve a problem every enterprise AI program keeps tripping over: how to talk about AI cybersecurity in the same control language as everything else. The draft Cyber AI Profile overlays “Secure, Defend, Thwart” onto CSF 2.0 outcomes, which sounds simple until you see what it forces you to inventory, log, and govern. If your org is doing AI without turning it into a parallel security universe, this is the blueprint NIST is testing.
AI Compliance Is Becoming a Live System
How long would it take you to show a regulator, today, how you monitor AI behavior in production? If the honest answer is “give us a few weeks,” you’re already behind. This piece breaks down how governance is shifting from scheduled reviews to always-on infrastructure, and offers three questions to pressure-test your current posture.