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I want to buy a wildcard SSL certificate to be used by multiple web servers. Is this possible? If so, what is the configuration?

DNS design for [www/nas].example.com:
A Record | @ | Shared Web Host
A Record | www | Shared Web Host
DNS Record | nas | Local NAS Server

1. Is it possible for two external servers to share separate sub-domains (i.e. nas.example.com for my NAS Server and *.example.com for my Shared Web Host)?

2. SSL providers give me a CA bundle. Do I install this CA to both servers?

3. Will Whoisguard protect both servers?

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  1. Is it possible for two external servers to share separate sub-domain...

There is no technical reason against installing the same certificate on multiple systems if the domains on the system are covered by the certificate. There might be usage restrictions by the CA which you need to check. And since all systems with the same certificate need to use the same private key the change of compromising the key gets larger.

  1. SSL providers give me a CA bundle. Do I install this CA to both servers?

Of course.

    1. Will Whoisguard protect both servers?

Whoisguard is about hiding the real owner of a domain from the publicly accessible whois information and has nothing to do with SSL certificates or on how many servers you use the domain.

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