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.
  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’
Proxy

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

Citrix rdp proxy

Level: Information

Keywords: Audit Failure

Rdp

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.