Step 1 – What You Need
A copy of Apache that includes SSL support.
A copy of OpenSSL.
An openssl.cnf file.
The copy of Apache that I had installed on my machine did not include SSL support, so I moseyed on down to the Apache download page. You’ll notice on that page that there are files named something like apache_2.2.11-win32-x86-openssl-0.9.8i.msi, as well as files named something like apache_2.2.11-win32-x86-no_ssl.msi. You need to have the openssl version installed, not the no_ssl version (duh). I couldn’t find any reliable info on manually adding SSL support to a no_ssl install, so I simply downloaded the most up-to-date version of the openssl installer and ran it. It successfully upgraded my version of Apache without overwriting any of my existing config files.
The nice thing about that installer is that it includes a copy of OpenSSL, so you don’t need to download that separately.
Finally, you need an openssl.cnf file, which doesn’t come with the package. I downloaded one that works from Neil’s site. If that link is broken you can find a copy attached to this blog post. I have Apache installed in C:\Apache\, which means that I can find OpenSSL in C:\Apache\bin\, so I copied the openssl.cnf file into that directory.
Step 2 – Create a Self-Signed Certificate
This step will create a number of files related to your certificate. Each of those files has the same name, with a different extension. In the example commands below I’ve used the name bob. Feel free to replace that with anything you like.