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For Apache it means configuring mod_ssl and generating either self-signed digital certificates, which the user needs to accept, or buying certificates from a global provider like VeriSign, GeoTrust, RapidSSL, Thawte, etc.
You will find more details about setting up and configuring Apache with SSL support in the deployment guide:
Check 23.8. Apache HTTP Secure Server Configuration.
For SSL based VPN, check https://openvpn.net/index.php/access-server/download-openvpn-as-sw.html
or http://openvpn.net/index.php/open-source/downloads.html for the free version.