Two years ago, I dove into the wonderful world of static blog generators when I left my TechNet blog behind and started using Jekyll to generate an Azure web site. With my newfound freedom from complex content management systems, I raved about Jekyll in a blog post. But once the honeymoon was over, some cracks started to appear in the relationship.
Jekyll does not officially support Windows, so you have to jump through some hoops to get it up and running. This didn’t seem so bad at first, but I’m one of those people who is constantly tinkering with my PC, buying new hardware, and upgrading things, so I end up doing a clean install of my OS several times a year.
Back in the day, a clean install of Windows might sound daunting, but these days, it only takes minutes. The Windows install itself is pretty fast, and I have several Boxstarter scripts that use Chocolatey to install all the software I use. This means getting back up and running is fairly painless - except for Jekyll.
It seemed like every time I got a clean install, that fresh new clean OS feeling was soon soured by errors from Jekyll. The hoops I had to jump through to get it up and running would change slightly each time due to changes in Ruby or problems with gems. For a while, I dealt with this issue by blogging from one of my Ubuntu VMs.