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Installing Wildcard SSL Certificate on Azure VM

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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?


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