I have converted this whole blog from Octopress to Hugo and modernised the theme.
I haven’t blogged in a while, and the prospect of getting Octopress to build on a modern machine had become its own deterrent. So before I could write anything, I had to do something about the platform. But I’m not sure I would ever have bothered until Claude Code made things easy.
The problem with Octopress
Octopress is built on Jekyll 0.11, released in 2012. The latest Jekyll is 4.x. Most of Octopress’s plugin ecosystem assumes APIs that no longer exist.
First I asked Claude to try and fix everything. Claude spent about two hours bringing the existing repo back to life. I saw it installing Ruby 2.7 alongside an MSYS2 toolchain, bumping and pinning dependencies. It did get everything working, I had a working Octopress install in 2026.
I’d made a mockup of how I wanted everything to look and used Claude Design to turn it into a design system. I got Claude to try to apply the new look to Octopress and it got about 80% of where I wanted it visually. But to get the last 20%, I’d have to rewrite Octopress’s templates wholesale.
Everything felt rather fragile and looked haphazard. I asked Claude for recommendations and it suggested moving everything to Hugo instead.
Picking Hugo
- The HTML of the mockup for the new theme I’d designed translates almost line-for-line to Hugo Go-templates.
- Hugo’s syntax highlighter (Chroma) is Pygments-class-compatible — the existing Solarized SCSS survives the migration unchanged.
- It’s still actively developed; Octopress hasn’t seen a release since 2015.
Porting the content
The hard part of any migration is the content. Octopress posts are Markdown files with YAML front-matter and Liquid shortcodes embedded in the body — {% codeblock %}, {% img right /p alt %}, {% blockquote author %}…{% endblockquote %}, {% youtube ID %}, some Octopress-specific like the {% pullquote %} and {% highlight TEXT %} plugins.
Hugo doesn’t speak Liquid. So Claude Code wrote a Python script that converted everything either translated to Hugo equivalents or rewrote to plain Markdown.
Blog resurrected
If you are reading this, it means it’s all working. A blog that was doomed has been resurrected. Thanks Claude.