I have finished migrating from an “old” virtual private server (VPS) running Windows Server 2008 to a server running 2012 r2 which includes IIS 8.5
At this time the 1.9.1 is the latest https://github.com/Lone-Coder/letsencrypt-win-simple/releases
After extracting the zip you need to move the content to a permanent folder from where you can keep running the Automated Certificate Management Environment (ACME) which can renew the certificates
If you run it as admin, it will ask you for your e-mail. It will stay private, it’s just to notify if a renewal failed.
Will you agree on https://letsencrypt.org/documents/LE-SA-v1.1.1-August-1-2016.pdf
next is a list, not of the websites but the bindings. Mine was rather big (100 entries) and contained multiple pages. After the bindings there are more options:
After selecting a “website” number you can specify the user which will be used to run the renewal process.
The last step is to make an entry in your calendar to verify that the renewal succeeded.
I have also installed Certify to view the certificates http://certify.webprofusion.com/
I used version Alpha V0.9.85
All that was left was to test the website with https and if it succeeds, make an IIS redirect to route all traffic to the https version:
Good luck and enjoy the free SSL certificates!