Observability Design for the AI Era — Reconciling PII Protection With AI Searchability, and Driving Self-Healing

Part 1 laid out four monitoring axes (application / infrastructure / CI / LLM) and the shape each one ends up in. Part 2 picks up where the data actually flows: it's production data, with PII in it. This post is about a multi-layer PII design that hashes at both write and search time with the same function, an integration surface where humans (web dashboard) and AI (MCP) share the same backend, and how all of that becomes the real driver of Self-Healing — running from CI failure to PR proposal end-to-end.

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