I've used https://github.com/Lone-Coder/letsencrypt-win-simple https://github.com/Lone-Coder/letsencrypt-win-simple to good effect; it's under active developmen

I've used https://github.com/Lone-Coder/letsencrypt-win-simple https://github.com/Lone-Coder/letsencrypt-win-simple to good effect; it's under active development, and has Azure DNS support. Doesn't help with Azure-hosted sites as such, but works great with IIS.