Until recently, it was not possible in Azure to host multiple SSL websites in a single IaaS VM (or load-balanced set of VMs), all listening on port 443 using different certificates (e.g. for separate domain names). People had to either use ARR farms in front of the web servers (making deployments more expensive and hard to manage) or use SNI (Server Name Indication) certificates, eliminating usage by all those brave people still running XP. This limitation was caused by the fact that a cloud service in Azure did only get one Virtual IP Address (VIP) from the fabric to get bound to port 443 for a single certificate.
Now, as Microsoft has announced availability of multiple VIPs per cloud service around Build 2015, it’s finally possible to configure several SSL endpoints, each of them pointing to a different website on the same VM (or set of VMs behind the Azure load balancer). This post will go through a simple example of setting up two SSL websites on a single VM.