Installing Octopress on Windows

Posted by nielsb on Wednesday, October 23, 2013

In an earlier post, I wrote how I had changed blog-engine from WordPress to OctoPress. At the moment I am running Windows as my main OS (mostly due to work related requirements), and - as OctoPress is very much Ruby and Python based - there are certain things to be aware of when installing this on Windows. Furthermore, my blog is now hosted on Windows Azure - so, with all this in mind, I thought I’d put together a blog post about the set-up of OctoPress on Windows, running on Windows Azure.


Before you begin the installation there are some pre-req’s:

Git and GitHub

Octopress is a developers blog engine, and central to everything Octopress is Git. Make sure you have the latest version of Git for Windows installed. You also need a GitHub account, so if you don’t have a GitHub account, you should sign up for one. While you probably will do most of the Octopress Git and GitHub related tasks from command-line, it will not hurt to have the GitHub for Windows UI application installed as well.


Octopress is built on Ruby, and when you eventually create blog-posts you will execute Ruby commands, so you need to install Ruby and the Ruby Development Kit. Octopress seems somewhat “picky” about what Ruby version to use, personally I am running version 1.9.3-p448, and it works fine.

You also need to install the Ruby Development Kit (DevKit) so you can use some of the native C/C++ extensions. Which version to download is dependent on the Ruby version, but I am running 4.5.2, DevKit-tdm-32-4.5.2-20111229-1559-sfx.exe.

After you have downloaded and installed both Ruby as well as the DevKit, you need to run two installation scripts for the DevKit:

  • change to the directory where the devkit is installed, and run: ruby dk.rb init.
  • then - still in the same directory - run ruby dk.rb install.

For more information about the installation of Ruby and the DevKit, GitHub has a great wiki page.


In addition to Ruby you need Python (this mostly for syntax highlighting). When installing Python, the version is very important. Download and install Python 2.7 from here.

Having installed all the above you should now be set for the actual installation of Octopress!!

Install Octopress

To install Octopress you need to clone the “original” Octopress repo from GitHub. From command-line you cd to the directory where you want clone the Octopress repo into, alternatively you create a directory for this and cd into it.

In the code below the assumption is that the directory exists and it is named MyGitHubRepos. As you can see from the code, after you have changed into that directory you clone the original Octopress directory into a new directory with a name of your choice. In the example below, the name is myoctopressblog.

$ cd MyGitHubRepos
$ git clone git:// myoctopressblog

After having cloned the original GitHub repo, you need to install a Ruby bundler. The Bundler maintains a consistent environment for Ruby applications, and you install it into the directory you cloned Octopress into (in the case above: myoctopressblog). BTW, gem is like a package installer:

$ cd .\myoctopressblog
$ gem install bundler
$ bundle install

By now your blog is almost 100% complete. What remains is an Octopress theme. For the initial setup, the default theme will do. To install this you run the equivalent of a MAKE file, a rake file:

$ rake install

Congratulations you now have an Octopress blog!! If you are curious what it looks like you can now run rake commands to generate and preview the blog pages:

$ rake generate
$ rake preview

After you have executed the rake preview command you can browse to localhost:4000 and see the blog in all its glory. If you did browse to localhost:4000, you can see that you have a very basic blog. By now you definitely want to configure the blog, and maybe also write - at least - a Hello World post.

Configuring Octopress and writing an initial post

The official Octopress site has very good documentation about all things Octopress. So, instead of me re-iterating everything about configuration and using Octopress for blogging, I rather point to the official documentation for configuration and basics about blogging with Octopress.

Right, by now you should have fairly good idea how to use Octopress - it’s awesome, right?! But … hang on a second, we are missing something - right; as awesome it is, the blog is still only on your local machine. So what do we do if we want to host the blog somewhere out on the interwebz?

Deploying Octopress

In order to get a fully functional blog, we need to host it somewhere, and with Octopress there are some nice and easy ways to deploy and host the blog. As with the secion about configuring the blog, I’ll let the official documentation do the talking for some of the ways Octopress can be deployed:

In order to publish posts to all of the options above you need to run rake generate followed by rake deploy after having written a post(s).

I mentioned up at the top how I was hosting this blog on Windows Azure, how is that done?

Hosting Octopress on Windows Azure

I initially thought I would host the blog on GitHub pages, and I did set up the blog to be deployed to my GitHub pages. Then, somehow, I thought that maybe I should check out Windows Azure - seeing that I have - through my work at Derivco - an MSDN subscription (Derivco rocks!), and the subscription gives me Windows Azure credits.

So, on to the wisdom of all world (Google), and lo and behold - there were quite a few posts / articles how to link a blog to Windows Azure. Seeing that I already published / deployed to GitHub pages it was extremely easy to push this to Windows Azure:

  • Set up a web-site through the Windows Azure portal
  • Configure the deployments to point to the GitHub pages

That’s all there is to it. Now after you have run rake generate and rake deploy, when you commit, the changes will be published to Windows Azure:

$ git add .
$ git commit -m "Some message about the commit"
$ git push origin source

Oh, I almost forgot - I also needed to point a CNAME for my domain to my website on Windows Azure. But, the whole Windows Azure setup took less than 10 minutes!!

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