Deploying ssl Certificates per site on iis

Question

I currently have several sites deployed on an iis 8.5 server, each site has its own 80 and 443 binding, i need to have different certificates for each one of the hostnames configured on the machine, however when i want to edit the cert associated to the 443 binding on one site, i get the following message:

At least one other site is using the same HTTPS binding and the binding is configured with a different certificate. are you sure that you want to reuse this HTTPS binding and reassign the other site or sites to use the new certificate?

Yes / No

This happens even though i have the hostnames set for each binding of each site,

If i hit yes, all bindings are modified and all sites remain with the same cert, and if i hit no, nothing happens,

How can i change the certs for just 1 of the sites i have hosted?

Answer 1

This can be achieved using Server Name Indication (SNI), and configuring it on IIS 8 (not available on previous versions)

after checking the server name indication checkbox you won't get the same message again

Server name indication ends up being the same as having virtual hosts on nginx or apache.

Example from editing Bindings for a web site in IIS 10:

Answer 2

You cannot, unless you have multiple IP addresses bound to your NIC. The host header sent per request isn't visible to your server, as such, it resolves which SSL certificate to use based on the IP requested - essentially SSL bindings are done against the IP, not the hostname (I know it doesn't look like that in the GUI).

Why do you want a certificate per site? Why not just get a wild card and set the host header per site?

Please see the question/answer here, essentially the same as what you're asking.