&gt; Jekyll should work on Windows because Ruby works on Windows.<p>Jekyll is a bit of a nightmare on Windows at the moment, at least if any significant part of your workflow is based on cygwin.  (I helped a colleague get it running a couple weeks ago.)<p>Cygwin ruby + gem install jekyll -&gt; fail.<p>rbenv to build ruby from source under Cygwin, gem install jekyll -&gt; fail.<p>The one solution I found that works is using Chocolatey [1] to install ruby and then gem install jekyll.  Even so, I wasn&#x27;t able to get pygments working for syntax highlighting, and the Chocolatey Ruby does not play nicely with cygwin terminal for interactive programs.<p>[1] <a href="https:&#x2F;&#x2F;chocolatey.org&#x2F;" rel="nofollow">https:&#x2F;&#x2F;chocolatey.org&#x2F;</a>