This was done on Windows 2012 Server R2. It has been a roller-coaster ride trying to get this server setup for remote access. I have had the ability to remote desktop locally on the network since day one, but we have a user that will need to connect using remote desktop from the internet. After searching and searching for an appropriate solution most of everything turned up that I should setup the RD Gateway service. So I installed that as well as the other services (licensing, web access, broker) just in case there were some dependent commands that would come up.
After the install for the features were complete I rebooted the server to finalize and started configuring all the services it would let me with a self signed certificate. No matter what I did though the RD Web Server certificate part would always fail saying"Unable to connect to server" but it IS the server. DNS entry number 1 is itself. But I don't need the web access, it would just be neat to have. So I tried to configure the RD Gateway- the real reason I setup this feature and it went through the install just fine. It said it succeeded and prompted me to setup the certificate, but I noticed that when I got to the certificate setup page that RD Gateway was grayed out. I closed out of that window and noticed that the RD Gateway icon still showed the green plus sign like it wasn't setup with the others. I right clicked it and it gave me the option to basically set it up again on the same server again. I did that, it said succeeded, went to the cert page, still gray, and the icon never updated. I can infinitely configure it to be the RD Gateway server but it never takes, but also never says there is an issue.
So I started thinking maybe this isn't what I need so I'll just remove this feature and do some research. I attempted to remove it and rebooted. Windows failed to remove the feature, and now I can't even remote into it locally. It says that "This computer can't connect to the remote computer". It sees it. It's prompting for login details when I input both the IP or the host name.
There were no red flags through the setup until the RD Web server said it couldn't find itself.