From the dawn of HTTPS-time, admins have struggled with setting up multiple SSL certificates on a single server. At the same time, we have Sitecore’s licensing model which really drives the business to get the most value out of fewer Sitecore instances. This leads teams to encounter multi-tenant installations that also require SSL protection, which in turn leads to me receiving questions like the following from clients:
“How do we get Sitecore to have multiple HTTPS websites on a single instance?”
The multiple SSL certificates problem is not because of a limitation on the Sitecore side, but rather a limitation in Internet Information Services (IIS). No amount of configuring Sitecore site definitions will help you solve this problem. So how do we solve this issue?