GitHub Pages (Jekyll) installation on Windows 7x64

Main install

1. Install Ruby 2.4.3 via RubyInstaller (not 2.5, conflicts with things later)
2. Let it install MSYS2 or do it yourself.
3. gem install bundler
4. gem install github-pages (this includes jekyll itself and is where things break most)
5. jekyll -v (3.6.2 at the time of writing, a little behind latest 3.7)
6. jekyll new myblog
7. Edit myblog/Gemfile to comment out jekyll line and uncomment github-pages line.
8. bundle install (in myblog)
9. bundle exec jekyll serve (in myblog)

Troubleshooting

MSYS2

I had random segfault on first install attempt, which went away by itself.

I was getting "invalid crypto" errors in pacman commands and had to set SigLevel = Never in c:\msys64\etc\pacman.conf for pacman -Syu to complete.

libcurl

I was getting 'Could not open library 'libcurl' errors inside jekyll-remote-theme and had to get libcurl.dll from this specific source and place into c:\Ruby24-x64\bin\ (via this SO answer, other libcurl.dll didn't work for me).

Chocolatey

Chocolatey initially installed Ruby 2.5, which conflicted with one of the gems, and downgrade to Ruby 2.4 broke Jekyll binary for me. Might have been sequence of events, but I just went to RubyInstaller on next attempt.

Jekyll Windows docs refer to Ruby DevKit, but with recent Ruby versions what you need is MSYS2 instead (as above).

They also refer to manually installing Nokogiri gem, but by now the kinks seem to be gone and it installs just fine with github-pages gem.