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