Comment by desiredpersona

In the past i too faced similar issues starting out (about 2 years ago) with Jekyll especially on Windows so i can relate.

I don't think this is the case anymore tho, as you can use two commands `brew update` to update Ruby and `bundle update` to manage Jekyll.

- Homebrew does a great job of managing Ruby versions on macOS.

- Bundler now manages all of Jekyll's dependencies without issue.