TL;DR
I had a feature branch that drifted five months behind main, and rebasing it produced 312 merge conflicts across 137 files. Instead of grinding through them by hand, I built a small triage harness that classified each conflict, handed the hard ones to Claude Code with the right context, and gated every batch behind a compile-and-test check. It took 11 hours instead of the two weeks I'd budgeted — and the failures taught me more than the successes.
The Problem
Every team has one of these branches. Ours was a storage-layer rewrite: started in February, kept alive by "we'll land it next sprint," and by July it was 5 months and 1,900 commits behind main.
The numbers when I finally ran the rebase:
