A really useful feature of Azure is that it can inject elements into the Role instances as it applies the configuration.
This is super, extra useful because all roles are sysprep’d images. This includes your VM Roles.
If you follow the Azure rules for creating your VM Roles you must prepare the VHD image with sysprep.
I don’t think this is very important if you only have one instance – but the Azure assumption is multiple instances of any role. With that assumption the use of sysprep applies.
The problem is certificates. If I sysprep my VHD I break the private key of my certificate as a new private key is generated.
The Visual Studio interface does not have a Certificates tab for the VM Role. However, don’t let this stop you. It is a simple edit of the Service Definition and the Service Configuration.
In the ServiceDefinition.csdef add a Certificate entry that names the certificate and the certificate store in which to place it.
<Certificate name="MyCertificate" storeLocation="LocalMachine" storeName="My" />
This example places the certificate “MyCertificate” in the Local Machine Personal store.
In the ServiceConfiguration.cscfg add a mapping entry for the certificate you added to your Azure Service and this Role.
<Certificate name="MyCertificate" thumbprint="8F4A08C8A0**************A**E482****CF4AB" thumbprintAlgorithm="sha1" />
This maps the thumbprint that Azure knows to the name you assigned the certificate to the store in which to place it. And since the certificate you load into Azure includes both the public and private keys the certificate is fully functional once the Role instance is provisioned.
Now, all this being described.. If you use a Web or Worker role – just use the Certificates tab in the GUI. Hopefully as the VM Role evolves, it will become as easy – for all the same reasons.