So I am new to using SSL certs on websites and have some questions..
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If I get a SSL cert I can use it on my main production web box and a clone failover box correct, I don’t need to get two different PFX keys or pay for two?
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I have two sites like this in IIS7.
a. http://www.kylesite.com
b. account.kylesite.com
They both need https but when I assign the SSL ceftificate in the http binding of the site it gives me this and I don’t know what to make of it or if I can use this same cert for my main site and subdomain site..

1) Yes you can export to PFX (include the private key), and import into a new box.
2) You need a unique IP:PORT combo in order to bind IIS to an SSL certificate.