So like I mentioned in my last post, I have migrated from WordPress to Jekyll as my content management system.

Initially I tried to install and run it on Windows.

Running Ruby natively on Windows is not something I would recommend for anyone that enjoys their sanity, in particular if you need to build gems.

It’s not impossible - it’s just difficult. You have to install a whole bunch of supporting plumbing and infrastructure to get everything working correctly, and these are the problem because finding native Windows equivalents is usually a challenge. Also, you may have to recompile some of this dependencies and the native tooling for Windows becomes an additional challenge.

After getting a huge number of cryptic errors I changed tack.

So I ended up running it on Ubuntu on the Widows Subsystem for Linux (WSL).

Works perfectly.

Now Jekyll is actually a bunch of Ruby gems, and as a good housekeeper I attempted to update them all to the bleeding edge.

gem update

However I got an error with one of the gems, OpenSSL.

When I tried to update it independently …

With the following details.

The (very un-intuitive) solution to this is to install some missing libraries.

sudo apt-get install libssl-dev

This will pull down and install the necessary libraries for the OpenSSL gem to be compiled.

Mission accomplished!

Happy hacking!