Everyone thinks migrating a codebase with AI means pointing a model at your files and saying "convert these."

That's not a plan. That's a wish.

Migrating a 10-year-old product isn't a refactor; it's an excavation. We had ~1,100 files deeply entrenched in Flow (last real release: 2019) that we had to safely move to TypeScript without breaking the app.did

Before writing a single prompt, we sat with why the "just let the AI do it" approach fails:

Context is bounded: Feed a model a slice of 1,100 interdependent files, and it's blind to the rest.