Discussion on "Structured output broke on us three times. Here is what the failures had in common."

jamesoconnor · 2026-06-22T08:13:20.933Z

TL;DR: Over the last 18 months I debugged three structured output failures in production agents. None of them surfaced as Pydantic errors. The schema was valid, the field types matched, and the agent

Discussion on "Structured output broke on us three times. Here is what the failures had in common." | Hashnode

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Structured output broke on us three times. Here is what the failures had in common.

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