Connecting to a Windows 2012 R2 RD Gateway server when you are behind a proxy server, especially one requiring authentication, may fail with the following errors:
‘Your computer can’t connect to the remote computer because an error occurred on the remote computer that you want to connect to.’
Or
RDP over HTTPS doesn’t seem all that neat but in previous iterations of terminal server or remote desktop from the RD Gateway page (connected over HTTPS) launching the rd client would make a new connection over a new port to the target terminal server. Even if you had changed the default rdp port the terminal server had to be listening on a.
‘Remote Desktop can’t connect to the remote computer for one of these reasons:
- Connecting to a Remote Desktop Gateway behind a proxy server. Hal Sclater 16th December 2015 Remote Desktop 0 Comments. Connecting to a Windows 2012 R2 RD Gateway server when you are behind a proxy server, especially one requiring authentication, may fail with the following errors.
- Apps on mobile devices and Microsoft's official Remote Desktop App on Mac OS X doesn't support ports for Remote Gateway. If you want to run OWA and have ActiveSync, good luck I doubt it would work. I have had issues with Reverse Proxy on Microsoft services not tending to be stable.
- Remote access to the server is not enabled
- The remote computer is turned off
- The remote computer is not available on the network’

Additionally, you will see the following event ID 4625 in the security log on the gateway server.
Log Name: Security
Source: Microsoft-Windows-Security-Auditing
Date: 8/5/2013 4:20:00 PM
Event ID: 4625
Task Category: Logon

Level: Information
Keywords: Audit Failure

User: N/A
Computer: RDGW.CONTOSO.COM
Reverse Proxy Rdp Gateway Download
Description:
An account failed to log on.
This issue is documented here:
To fix it, set the EnforceChannelBinding registry value to 0 (zero) to ignore missing channel bindings on the Gateway server.
HKLMSoftwareMicrosoftWindows NTCurrentVersionTerminalServerGatewayConfigCore
Type: REG_DWORD
Name: EnforceChannelBinding
Value: 0 (Decimal)
Reverse Proxy Rdp Gateway Login
Note By default, the EnforceChannelBinding value does not exist on the Gateway server. You must create this value. When you are done, reboot the server and it should work behind your proxy server.