Migrating this site from Jekyll to Astro

Planted 02026-03-24

How AI and OpenCode made this migration possible in one session.

They did it by making the single worst strategic mistake that any software company can make: They decided to rewrite the code from scratch.

— Joel Spolsky, Things You Should Never Do, Part I

I had relented this site to forever being built with Jekyll and fighting Ruby and gem version issues for the rest of my life. However, with AI and OpenCode, I migrated this site from Jekyll to Astro.

Jekyll is ol’ reliable but I don’t use Ruby as much as I might like to. The setup overhead was not great. The remote deployment story was not great, build locally and push to remote always works great though. I also love Vite and TypeScript.

I gave myself a few non-negotiables. Cool URLs don‘t change. No large markdown change required. Keep deploy simple.

A few hard parts:

• Liquid leakage: some markdown that used to pass through Jekyll started rendering raw Liquid and Kramdown artifacts.
• Style regressions: pages like /booklist/, /wanttoread/, /notes/, /principles/, and /forthefirsttime/ needed route-by-route parity fixes.
• Cloudflare edge cases: deleting the old Pages project required deleting a large deployment history first; custom-domain cutover for www required removing conflicting DNS records.

From this migration session:

• Total session time to merge: 8h 17m 40s
• User prompts: 71
• Assistant turns: 1,011
• Merge span: 4 commits
• Net repo diff in the merged migration: 159 files changed
• Lines changed: +16,136 / -6,719

The site now runs on Astro and deploys to Cloudflare Workers. Away from Jekyll and Cloudflare Pages.

Both lukasmurdock.com and www.lukasmurdock.com are served through Workers custom domains, and the old Pages project is gone.