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We have a wildcard SSL cert for example.ca, sites running example.ca have SSL setup and working. We recently got the .com domain and we are considering purchasing another wildcard SSL cert for the .com

I know that there are issues with virutal hosts and multiple SSL site however is it possible to have two SSL certs inside the same VirtualHost? So if someone goes to example.ca or example.com they get a cert for both and no warning?

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No. Apache can only associate 1 SSL certificate with any given IP/port combination.

This is because the SSL negotiation occurs first, and only once the security has been established does HTTP start flowing. The name of the requested site is part of the HTTP requests. In other words, when the client connects to port 443 on 1.2.3.4, Apache must give it the relevant SSL certificate without knowing what site it wants.

There is an extension called Server Name Indication which allows for SSL/TLS clients to provide include the name in the initial SSL/TLS handshake, but SNI has not seen significant adoption, its biggest drawback at the moment being the complete lack of support for it on any version of IE running on Windows XP.

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