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Remote Desktop Gateway not Connecting to client computer (Authentication Successful but no RDP established)

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I have a new RD Gateway configuration that is failing to open the RDP session. The remote computer is able to connect to the gateway and a successful security audit is logged but the session never starts, giving the error:

Remote Desktop can't connect to the remote computer for one of these reasons:

1)Remote access to the server is not enabled

2)The remote computer is turned off

3) The remote computer is not available on the network

The Gateway server is on the internal network with 443 forwarded from the internet, the default web page is visible when connecting to the external address using HTTPS. There are no firewalls between the Gateway and the remote computers so all ports should be available there. Windows firewall is open for Remote desktop on both systems (Gateway and remote).

The authentication is successful for the Gateway box but it never seems to reach the endpoint system, there are no logs of any authentication attempts on the remote computer.

There are no sessions in the Gateway to monitor since it never actually opens RDP. 

The traffic just seems to die once it hits the gateway.

Any thoughts?


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