The best least failure-prone way I've found is by using RubyInstaller builds. Go to http://rubyinstaller.org/downloads/ to get the latest Ruby+Devkit (be careful to choose well your architecture). gem install jekyll bundler If you have to create a new Jekyll app: jekyll new appdir cd appdir Finally: bundle install bundle exec jekyll serve 2020-04-24: Removed update of `Gemfile` to add `wdm`, `jekyll new` adds that already.