Practice · 2023–now · AI Present

AI will rewrite the codebase

Big-bang rewrite, now with a chatbot — then with agents. Same failure mode; prettier slides.

AI rewrites fail for the same reasons manual ones do: unknown edge cases, missing tests, and political ownership of legacy modules. LLMs accelerate typing, not accountability. Strangler migrations still win; autopilot and agentic-migration slides still lie.

Cost of the fad

Exec decks promised autonomous migrations "by next quarter," then rebranded as "agentic modernization." Teams that skipped tests, ownership, and incremental strangler patterns bought expensive demos and fragile diffs.

Case studies

Patterns

Context

Demos consolidate; evals remain

AI pair programming changed how code is typed faster than how it is reviewed. Agent frameworks and standalone vector stores sorted into demos versus durable plumbing; mid-market RAG folded back into Postgres. The permanent layer is familiar: evals that gate deploys, model routing for cost, tool protocols instead of plugin snowflakes, and humans who own production. Autopilot rewrites and vibe-shipped auth middleware are still big-bang migrations with better slides — and a longer on-call.

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