I have to say that I am not the absolute specialist and I have just set up my own XAMPP 1.4.14 (tried Linux and Windows) to have I private little Wiki using Mediawiki with encrypted communication between browser and server (hence - SSL). I am using a self certified certificate.
My steps to success:
1) Look on http://www.openssl.org/docs/HOWTO/
. You will find "certificates.txt" and "keys.txt"
2) Open "keys.txt" and you will find how to create your RSA private key which you will need to create a certificate (remove the -des3 option as described to avoid having to provide a password every 2 secs):
openssl genrsa -out privkey.pem 2048
Rename the generated privkey.pem to mykey.key and move it to [XAMPPDIR]\apache\conf\ssl.key\
3) Now open "certificates.txt" and create a (self-)certificate according to the instructions:
openssl req -new -x509 -key privkey.pem -out cacert.pem -days 1095
You will need to provide some information which is not really important in a self certificate but if somebody accesses your site later on they will be able to see it, so don't be rude... The "Name" bit is probably best set to your domain name such as www.test.org
Rename the generated cacert.pem to mycert.crt and move it to [XAMPPDIR]\apache\conf\ssl.crt\
4) In XAMPP SSL is already enabled so you do not need to edit httpd.conf. edit [XAMPDIR]\apache\conf\ssl.conf.
SSLCertificateFile "C:/Program Files/xampp/apache/conf/ssl.crt/server.crt"
SSLCertificateKeyFile "C:/Program Files/xampp/apache/conf/ssl.key/server.key"
5) Restart XAMPP (either use Link in start menu or if installed as service restart service)
6) In your Browser try https://myserver
and it should warn you about some "dodgy" certificate namely: yours.
7) Be aware that this is only a way of trying out SSL and I am not an expert so I might have missed important security issues... But it's fun!!