[mediumdave]

> Jekyll should work on Windows because Ruby works on Windows.

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.)

Cygwin ruby + gem install jekyll -> fail.

rbenv to build ruby from source under Cygwin, gem install jekyll -> fail.

The one solution I found that works is using Chocolatey [1] to install ruby and then gem install jekyll. Even so, I wasn't able to get pygments working for syntax highlighting, and the Chocolatey Ruby does not play nicely with cygwin terminal for interactive programs.

[1] https://chocolatey.org/