Governing self-classified documents at scale
Series
Governing self-classified documents at scale
How a two-agent LLM system caught underclassified, sensitive financial documents before they became a security incident — and the design decisions that mattered more than the models themselves.
A case study in document classification governance. If you want the transferable lessons without the ML detail, start with the disclosure problem in Part 3 and the rollout metrics in Part 4.
- Applied ML
- Agentic systems
- Security/Governance
- Model distillation
- RLHF

- Part 1
The self-classification problem
A structurally unenforceable policy, systematic underclassification at thousands of documents a day, and why keyword matching was never going to close the gap.
- Part 2
A two-agent system, and the trade-off that shaped everything
Why one model wasn't enough, how classifier and verifier agents split the work, and the distillation and RLHF loops that kept cost and behavior in check.
- Part 3
The two problems that almost broke this
Grounding model claims in real document lines, and the paradox where the classification system itself became the disclosure it was meant to prevent.
- Part 4
Rollout, results, and what I'd change today
Phased deployment across three stages, an 85% reduction in underclassification, and what I'd rebuild differently with today's models.