Network diagram: I have a moodle (a VLE) setup that I want to be internally and externally accessible. The green route on the diagram below is the route I would like the traffic to take when the user is inside the LAN, and the red route is seemingly what it does take. The website has a domain name (like most websites do). From the User PC, if I ping the domain name, I get the internal IP of the webserver (because of a hosts file entry), if I nslookup the domain name I also get the internal IP of the webserver (because of an A record on my DNS server). Running the same two commands on the webserver gives me the webservers external IP. (going well so far) If I use PHPs gethostbyname() on the moodle website and use domain name as a parameter (getting php/apache to resolve the hostname) it returns the exernal IP of the webserver (good news, DNS seems to be doing what I want it to). All things so far seem to be going well. The only thing that is confusing me and preventing the moodle single sign on from working is the fact that if I get moodle to show my IP address, it says that it is an external one (outside my NATting firewall) when it should show an internal IP. This is the issue, any ideas on how to go about resolving this? Any ideas on tests I can perform (I have also tried a tracert and the request goes directly to the webserver), anything? Thanks all!