Please fill out the fields below so we can help you better. Note: you must provide your domain name to get help. Domain names for issued certificates are all made public in Certificate Transparency logs (e.g. crt.sh | example.com), so withholding your domain name here does not increase secrecy, but only makes it harder for us to provide help.
My domain is:
I ran this command:
It produced this output:
My web server is (include version):
The operating system my web server runs on is (include version): SBS 2011
My hosting provider, if applicable, is:
I can login to a root shell on my machine (yes or no, or I don't know):
I'm using a control panel to manage my site (no, or provide the name and version of the control panel):
The version of my client is (e.g. output of certbot --version or certbot-auto --version if you're using Certbot):
I think you will be better served using a client designed for Windows systems. The most popular gui based client is Certify The Web. I found this post on their forum from 2 years ago for SBS 2011. So perhaps some hope.
It is probably best to post directly on that forum for CTW. Other volunteers may post other ideas here. Good luck.
SBS is not your problem.
The biggest problem you face is IIS < 8, which won't support SNI.
So, unless you plan on only ever serving one single public site via IIS...
You will need to upgrade IIS.
Uses another web server, in front of IIS (as a reverse proxy).