We have an IIS server running a website with HTTPS access on the server already.
We need this server to provide remote desktop gateway services to other servers on the network.
Today I installed Remote Desktop Services. I used the same certificate used for the website. After I finished the installation, I got an error from IIS that somebody else is using port 443 (SSL) and the website cannot use the binding anymore.
Of course, that was the Remote Desktop Gateway using the binding.
Is it possible to use both services on the same machine? (one IP, one interface only) as I understand Remote Desktop Gateway must use port 443?
What I did eventually is encrypt and tunnel the RDP connections on both servers according to this guide (using Putty and Copssh). We log in to the internal machines by RDPing into them from within the Webserver itself (We understand the risk here).
I also wrote a batch file to automate the login procedure. The script will terminate automatically upon logging off from the internal machine. (note: the ping command delays the remote desktop menu, thus giving the user enough time to enter the SSH password):
start /b putty <user-account>@<ip-address> -L <local-ssh-port>:<ip-address>:3389 ping 18.104.22.168 -n 1 -w 12500 > nul mstsc /v:localhost:<local-ssh-port> /f taskkill /f /im putty.exe
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