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How would I self assign a SSL Cert on Apache (XAMPP) on a Windows 2003 server? I have researched and the farest I got was a broken SSL Cert with "Common name" problem.

Post your guide or links here,

Thanks.

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What guides did you already follow? Did you double check you followed them to the letter? Getting these things working can take a few attempts. – dunxd Oct 20 '10 at 9:40
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Try http://www.sslshopper.com/article-how-to-create-and-install-an-apache-self-signed-certificate.html

You may need to adjust the paths and config files for your installation of XAMPP.

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