I have had RD Gateway working with self generated certificates every 6 months on our 2008 r2 server allowing windows 7 clients to connect from home to their windows 7 machines at work. Now I have had to add another website (forwarded to another machine - still just the default site in IIS on the rd gateway machine) and they want that one to use the defaults of 80 and 443. I changed the ssl bindings in IIS Manager to 82 and 444. This required me to update the home windows 7 clients rdp to v8 so they could specify a port. I thought I had all working fine but over Christmas break I could not remote in from home to check on things. I figured the server probably wasn't happy about something and a reboot would fix it but I wasn't that lucky. I have been trying all day to get it to work again.
I can connect to the home computers from work but trying to connect to work computers from home generates the error: "Your computer can't connect to the remote computer because an error occurred on the remote computer that you want to connect to." Looking in the IIS Manager settings in the Server Manager I see the only site (default) is not running. Clicking Start fails with: "The process cannot access the file because it is being used by another process". Checking SSL bindings I see https / 443 is back in the list. I remove it and now I can start the website okay. But I still get the same client error.
Checking the RD Gateway Manager I now see a red flag "A server certificate is not yet installed or selected". So I generate and import another 6 month certificate and install it on a client as well. That resolves that error and everything looks fine with the RD Gateway again. But the client still gets the same error.
Looking back in the IIS manager I see the default web site is again stopped and https port 443 is again listed at the end of the list of bindings. So, it's a neverending loop. As soon as I remove 443 from the bindings and start the site, the RD Gateway says there is no certificate installed. As soon as I re-import the certificate (or make a new one.. it doesn't matter) 443 is listed again in the IIS manager and the site won't run.