Here's a great piece of free software for IIS administrators who want to easily manage their SSL certificates from Let's Encrypt.

win-acme is a self-guided command line utility that allows you to quickly and easily take an IIS website and get an SSL certificate on it. After struggling with utilities like ACMESharpCore, ZeroSSL's Crypt-LE, and Posh-ACME, I realized that all of these tools, while powerful, didn't have any ease of use whatsoever. When I first looked at the text interface for win-acme, I didn't think it was going to be as easy as selecting options from a menu.

It's as easy as selecting optinos from a menu.

Within 5 minutes, I had 7 websites with shiny new SSL certs, and I had gotten them scheduled them for a regular renewal. I didn't have to do any configuration or any PowerShell scripting, it just worked. Give it a try if you're running websites on IIS!