Installing Wildcard SSL Certificate on Azure VM

Question

I'm developing an application on Azure VM and would like to secure it by using the wildcard SSL certificate that I'm already using with my main domain. The SSL cert works with any *.mydomain.com and the application on Azure VM is accessible through myapplication.cloudapp.net

Based on the research that I've done, CNAME should be the best option to do that (I can't use A record since we need to shutdown the VMs every week and turn them back on the next week and will lose the ip addresses).

My two questions are:

How can I have myapplication.cloudapp.net be shown as subdomain.mydomain.com?

Will doing that make it possible for wildcard SSL certificate to be used for Azure application too?

Answer 1

How can I have myapplication.cloudapp.net be shown as subdomain.mydomain.com?

Yes - this is just the CNAME forwarding and ensuring that the appropriate SSL certificate is installed on the server.

Will doing that make it possible for wildcard SSL certificate to be used for Azure application too?

Well as you're already exposing the Application through the VM - this should happen seemlessly.

Just a word of caution, you mention that you're using the certificate on the main domain, but haven't mentioned where you're using this. Be aware that, out-of-the-box, you can only assign one SSL per HTTPS endpoint. You can enable multiple SSL certificates on an Endpoint for Azure / IIS using Server Name Identification and can be enabled directly or automatically. If you do take this route, remember to configure your SNI bindings first, then apply the default binding - it kinda screws up otherwise.