Checkout Certify for automated IIS integration
For simple and automated IIS integration checkout Certify - http://github.com/webprofusion/certify
I've been using it on a couple of servers and it's been working great. If you click the 'configure auto renew' button it sets up a scheduled task to automatically renew your certs.
It's a GUI for ACMESharp (https://github.com/ebekker/ACMESharp) which is a bunch of tools for let's encrypt/IIS if you prefer the console way.
Biting the hand that feeds IT
