Ah good mention, didn't know about this tool. Looks very sleek!

I wanted to avoid building a solution to do the whole communication as I was pretty happy with the website functionality. This tool is mostly to enable you to use the website on windows and to automate a lot of the annoying Windows stuff while still retaining the option to use the website or the Let's Encrypt client in a pinch :)

Seconding that tool, but be sure to read all of the relevant Wiki pages before you use it, and if your IIS is hosting multiple sites do not miss:

https://github.com/Lone-Coder/letsencrypt-win-simple/wiki/HT...