Staging environment
Free Lesson

Find the telemetry your air-gapped AI is still sending

Hosted by Thomas Underhill

Thu, Oct 8, 2026

3:00 PM UTC (30 minutes)

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Where the Data Can't Leave: Self-Hosted AI for Regulated Industries
Thomas Underhill
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What you'll learn

Check the three properties an air gap actually requires

Isolated weights, disabled telemetry, controlled updates. Most deployments hold two and claim three.

Find outbound traffic your stack sends without being asked

Updaters, crash reporters, and a dependency three levels down with analytics on by default.

Test whether your deployment survives losing its registry

Cut the mirror and run a full deploy. Whatever breaks was never controlled, it was only reachable.

Why this topic matters

Most teams running self-hosted AI believe it is isolated. Almost none have checked, because the check is not obvious and nothing fails when it is skipped. The weights are usually fine. What leaks is a crash reporter nobody chose, an updater nobody disabled, or a dependency three levels down with analytics on by default. Your auditor is unlikely to test this claim, which is exactly why you should test it first.

You'll learn from

Thomas Underhill

Product & Eng Leader (AWS, VMware, HashiCorp, NGINX) · Adjunct Professor

I build and operate AI systems in places where you have to prove things: that the data never left, that the model did what you say, that a person approved the action.

Constellation is a self-hosted platform I architect and maintain: authorization on every tool call, pluggable secrets and sandboxing, a tamper-evident audit trail, local inference, sealed and air-gapped by default. My research is on evaluation that cannot be gamed by whoever benefits from the score.

Twenty five years in enterprise software before that, in senior roles at PayPal, Oracle, VMware, HashiCorp, F5 and AWS, running SOC 2, PCI-DSS, FedRAMP and NIST 800-53 as engineering programs, not paperwork. Nine years as adjunct faculty at universities. U.S. patent. J.D. Startups.

Everything I teach, I have had to make work first.

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