Troubleshooting Remote Desktop Gateway (formerly known as tsgateway)

Rather than provide portable computers for staff, the culture at my day job is for people to use iPads and other data consuming devices to remote back to their office desktop computer and do *all* their work.  Since leaving 3389 (the common Remote Deskop {RD} or Terminal Services {TS} TCP port) open to the Internet guarantees a bunch of door-knocking probes, we force everyone through the VPN or to use Microsoft’s RD Gateway.

With Windows Server 2008 Microsoft introduced TS Gateway (renamed RD Gateway with 2008R2).  You connect to the gateway over TCP port 443 (also gets around the common coffee-house WiFi limits on connecting to only web pages) and the gateway makes the 3389 connection to your workstation inside your campus/building/office network.

Clients are somewhat limited: Windows XP can use gateway with version 6.1 of Remote Desktop Connector.  Windows 2008, Vista, 2008 R2, Windows 7 all support RDGateway natively.  There is no Macintosh client (to my knowledge… Microsoft’s client and CoRD that I use both lack this capability) nor is there a xNix RD client with gateway connectivity.  On the iPad there are PocketCloud and iTap.

Client error messages are less-than-specific, unfortunately.

You will get the following message under two scenarios,

  1. You’ve entered an incorrect DNS name or IP address
  2. Name or IP address is correct, but no device is responding to 3389TCP connection by the RDGateway… which means either powered off or the machine is firewalled in a way that it doesn’t reply to the connection request from the gateway.noDNS

Another scenario, not unique to using a gateway, is attempting to connect to a machine with a user account that isn’t authorized (usually, isn’t in the Remote Desktop Users security group on that workstation).noAuth

The final scenario I have is if your RDGateway is down, you have no route to it, or you simply fat-fingered the host name:rdgUnavailable

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