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I have two Windows 2008 R2 servers which will be hosting a load balanced website. I will generate a private key and use it to generate a CSR using OpenSSL.

How can I make this CSR (or the resulting certificate) work for both servers? I assume I have to load the private key I used to generate the CSR on to both servers. If so, how do I do that?

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    Basically, yes. ;-) Posting this as a comment because I have no idea how you do this on "Windows". (IIS, I assume?) The CSR is what you give to the CA asking for a certificate. The general steps are (1) generate CSR, which can be done with or without generating a keypair (see openssl req --help), (2) get signed certificate, (3) place signed certificate and private key on both servers. (You should only need one CSR, as long as you copy the private key and the certificate that results from the signing process onto both servers.)
    – mpontillo
    Jun 14, 2012 at 1:02
  • ok so thank you for confirming what I thought was correct..the part I need now then is how to import a private key into IIS7? I've searched Google but found no good explanation...
    – blizz
    Jun 14, 2012 at 1:21
  • Never done it before, but a quick Google search shows that Windows uses PFX files. If you have OpenSSL-format keys they can be converted.
    – mpontillo
    Jun 14, 2012 at 1:40

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This depends if you use a Apache or IIS webserver.

If you use apache, just copy the private and the public key on the second server and configure it like described here http://tud.at/programm/apache-ssl-win32-howto.php3

If you use IIS, I assume you have to export the certificate including the private key via the windows certificat store. Have a look here http://nl.globalsign.com/en/support/ssl+certificates/microsoft/all+windows+servers/export+private+key+or+certificate/

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