Install Jekyll on Windows 10 - diev/diev.github.io GitHub Wiki

Based on http://jekyll.tips/jekyll-casts/install-jekyll-on-windows/ as the most modern post.

Chocolatey

Run cmd as Administrator (every time below!)

@powershell -NoProfile -ExecutionPolicy Bypass -Command "iex ((new-object net.webclient).DownloadString('https://chocolatey.org/install.ps1'))" && SET PATH=%PATH%;%ALLUSERSPROFILE%\chocolatey\bin

Check: choco /?

Chocolatey v0.10.3

Ruby

Close and run again

choco install ruby -y

Check: ruby --version

ruby 2.3.1p112 (2016-04-26 revision 54768) [x64-mingw32]

Ruby SSL work-around before the next step

Info: http://guides.rubygems.org/ssl-certificate-update/#installing-using-update-packages

Download https://rubygems.org/downloads/rubygems-update-2.6.7.gem

gem install --local %userprofile%\downloads\rubygems-update-2.6.7.gem
update_rubygems --no-ri --no-rdoc
gem uninstall rubygems_update -x

Jekyll and GitHub

gem install jekyll github-pages

Note: If behind some Internet proxy, use gem install --http-proxy http://domain%5Cuser:password@server:port jekyll github-pages or add SET HTTP_PROXY=http://%USER%:%PASSWORD%@%SERVER%:%PORT% to gem.bat constantly.
If that password contains i.e. @, replace it with %40 and so on.
If that proxy is NTLM, install http://www.telerik.com/fiddler on the localhost and/or browse http://stackoverflow.com/questions/4418/how-do-i-update-ruby-gems-from-behind-a-proxy-isa-ntlm for other solutions.

Check: jekyll -v

jekyll 3.3.1