Installing Jekyll on windows 8.1

Table of Contents

Alt “Jekyll Logo”

Jekyll is an static site generator designed for static websites and blogs. In this post, I enumerate the process of installing Jekyll on Windows 8.1.

On previous ocassions, my posts (though rare) have been dynamic and created using blogging platforms which make writing blog posts a very easy process. Unfortunately I never kept pace with the updates on these platforms and one day I woke up to find my site had been hacked. I panicked and decided to take down the site instead of trying to figure out what evil code had been injected into the site.

After the experience, I realized that disadvantages of using third party blogging platforms outweighed the advantages. Most blogging platforms rely on plugins and some plugins are not updated regularly. Yes, the plugins/modules were simplifying my work but none was available that did not have some open issues or minor bugs. Any plugin I added was only increasing the surface area for security attacks. I therefore decided to seek for a safer option that would require minimal updating.

Jekyll stores content locally in simple markdown text files which can be edited using any text editor. This makes versioning possible for the changes that I make to these files. By using simple text files, and letting Jekyll generate static sites from them, my maintenance requirements are totally minimized. I have no server-side language or databases to worry about. No XSS or sql injection to look out for. I may not be totally safe from those bad elements but at least I have minimized the surface area for attacks.

One of the powerful features of blogging platforms is their commenting systems. With Jekyll, your options are limited to either totally forgoing comments, using third party commenting services like Disqus, using social networking services like twitter, using a special per-post e-mail address to receive comments or incorporating a static comments plugin. If I was to make a choice, I would pick among the last three. But for now I will just forgo comments.

  1. Install Ruby

    • Download RubyInstaller for windows. I am using an x64 computer so I download rubyinstaller-2.1.5-x64 which is the latest x64 version.
    • After the downloadd completes, I start the installer and click OK to accept English as the default setup language
    • Accept license and clicked Next>
    • Modified suggested folder from C:\Ruby21-x64 to C:\Ruby2-x64.
    • Checked Add Ruby executables to your PATH and Associate .rb and .rbw files with this Ruby installation and click Install button
    • Click Finish after installation is complete
  2. Install Ruby DevKit

    • Download version which corresponds to installed rubyinstaller

    • Extract files to a folder of your choice. I opt for C:\RubyDevKit\

    • Initialize the DevKit and bind it to Ruby installation

      • Start up windows command prompt
      • Change directory to your DevKit folder. C:\RubyDevKit\
      • Auto-detect Ruby installations and installations to a configuration file by executing the following command
        ruby dk.rb init
        This creates config.yml file and adds a line on Ruby installation location. - C:/Ruby2-x64
      • Install DevKit binding to Ruby installation by running ruby
        dk.rb install

      Alt “Ruby and Ruby DevKit installation command window”

  3. Install the Jekyll Gem
    RubyGems is a packaging system that makes it simple to install Ruby libraries and Jekyll comes as a Ruby Gem

    • In the command prompt run the following command gem install jekyll

    • Pressing the Enter gives the following error

      ERROR: Could not find a valid gem 'jekyll' (>= 0), here is why:
      Unable to download data from - SSL_connect
      returned=1 errno=0 state=SSLv3 read server certificate B: certificate
      verify failed (

      Alt “Jekyll SSL certificate install error”

    • A bit of searching reveals the problem is documented.

      • I need to install using updated RubyGems. So in the command prompt type command to check for version

        gem --version

        This displays I am having version 2.2.2

      • Add new ssl certificate to currently existing certificates

        • Download new ssl certificate making sure file is saved with .pem extension

        • Locate RubyGems ssl certificate directory for current installation using the following command in the command prompt

          gem which rubygems
          This displays `C:/Ruby2-x64/lib/ruby/2.1.0/rubygems.rb`
        • Copy downloaded certificate to C:\Ruby2-x64\lib\ruby\2.1.0\rubygems\ssl_certs folder copy c:\Temp\AddTrustExternalCARoot-2048.pem C:\Ruby2-x64\lib\ruby\2.1.0\rubygems\ssl_certs

      • Re-run command to install jekyll

        gem install jekyll
      • And everything now runs smoothly Alt “Install Jekyll command prompt screen”

  4. Install a code snippet syntax highlighter

    You have an option between Pygments which requires installation of Python and Rouge which is purely written in pure Ruby. I opt for Rouge.

    • Run the following command in the command prompt
      gem install rouge
    • Set Rouge as the syntax highlighter
    • Navigate to DevKit root folder
    • Open _config.yml
    • Add the following text
      highlighter: rouge
  5. Add source folder changes watch

    • Run the following commands in the command prompt

      gem install wdm
  6. Type the following command to update installed gems
    gem update

    During update, some gems may have conflicts with locally existing gems and you may be requested to overwrite the executables. Always confirm by typing y to overwrite.

  7. Generating a new Jekyll site

    • Open the command prompt

    • Type the following command and press the enter key

      jekyll new <sitename>

      Replace <sitename> with your site name. Therefore for this site I will issue the command jekyll new site

      This will create a folder at the current location with a name of your <sitename>

    • Open _config.yml under root of your site and add the following text highlighter: rouge

  8. Testing the new site

    • Navigate to the root of the site folder

    • type jekyll serve <newsite> and press Enter

      Alt “Jekyll Server screen”

    • In your web browser, navigate to localhost:4000 and you should now see default website generated by Jekyll.

  9. After the build process, Jekyll creates a _sites folder. All that you have to do is to copy all files in _sites folder to your web server.

Run Jekyll on Windows