Hey Jamie!

I did write at the time an article about signing it:

How to sign an SSL Certificate using Let’s Encrypt on Windows Server?

Try certbot renew and see where you get stuck. I don’t have an exact guideline for you but I do remember that on Windows I had to edit a python file at some point to make it work.

Try certbot renew on the PowerShell and see where that gets you.

Once it works, I’m sure you can find a cron-like feature on a Windows server. My focus with ArcGIS has shifted to disconnected environments so I haven’t done the research for that.