Structured output broke on us three times. The third time taught us operator-ready.

Structured output broke on us three times. The third time taught us what "operator-ready" means.

Last quarter we shipped a contract-extraction agent to an enterprise legal team. Schema validation passing at 97%. Human reviewers satisfied with the output quality in testing. Rollout went smoothly.

Then it broke. Three times. In three completely different ways.

The first two failures we fixed with better prompts and stricter schemas. The third one taught us something the first two hadn't: that "operator-ready" is not a technical checklist. It's a claim about your agent's behavior under conditions you didn't design it for.

Failure one: the validation paradox