HTTPS on Azure Virtual Machine

Question

I am moving our web site to Azure, running on a Windows Server 2012 VM. I have purchased a wildcard SSL cert from GoDaddy and it has been installed and configured on the VM. I have also configured IIS to utilize this cert for all requests on port 443. I have also created the HTTPS endpoint in the Azure management console on port 443.

I can connect just fine to the web site on port 80, but 443 cannot be reached and monitoring the connection through fiddler, I'm getting a 502 response.

I have searched all the documentation on Azure and cannot find much help for setting up SSL on a virtual machine in the cloud.

Answer 1

Make sure you open up the endpoint for 443 to route it through to your VMs. See http://www.windowsazure.com/en-us/develop/net/common-tasks/enable-ssl/

Answer 2

When I set up the endpoint for SSL, I had checked the box for "Enable Direct Server Return." This setting prevented SSL from working. I haven't come across any documentation explaining why it behaves this way. Removing the endpoint and creating it without direct server return enabled fixed the problem.