I have done a new install of Debian Jessie (8.5) with ISPConfig (18.104.22.168p9), and Apache (2.4.10). I am having an issue making changes to the website after I have already created it. For example, I setup the website before I had more IP Addresses. Once I had more IP Addresses I added them to the servers network config, added them to the Server IP Address list under System (also checked the box for vhost), and added them to the websites as needed. The ones that I had already made do not reflect the changes in the vhost and do not see to work with the new IP Address. If I create a new one with the extra IP Address, it works fine. I am not sure if there is a bug in ISPConfig that is causing it to fail to update the website vhost or if there might be an issue with the version combo I am using. As a side note, if I restart Apache from the console I get an error about NameVirtualHost being obsolete and will be removed in future versions. It seemed ISPConfig used this for updating the sites as it adds the IP Addresses to the config file when I added them with vhost option. The error doesn't stop the system from starting, just something to note for future releases.