Windows 8 Unable to Connect through RD Gateway

A customer of mine today logged a support case stating users on Windows 8 or Windows 8.1 were unable to connect to remote computers by using a Remote Desktop Gateway (RD Gateway).

I tested this functionality and was able to reproduce the issue.  The error experienced was:

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
Make sure the remote computer is turned on and connected to the network, and that remote access is enabled.


Windows 7 clients did not receive any problems connecting through an RD Gateway.

After reviewing the group policy applied to the domain, I noticed a Group Policy object was setting the LAN Manager Authentication Level to "Send LM & NTLM - use NTLMv2 session security if negotiated".

 
The new RDP 8.0 client (built into Windows 8 and 8.1) requires this policy be set to "Send NLTMv2 response only" as it uses NTLMv2 and does not have the ability to negotiate authentication.  "Send NTLMv2 response only" is the default for Windows 8 and Windows 8.1.
 
As a test, I set a local policy on one of the Windows 8 computers using gpedit.msc and then did a gpupdate /force followed by a reboot.
 
 

After setting the LAN Manager authentication level to "Send NLTMv2 response only" I was able to connect to RD Gateways without issues.

I did not test this, but I assume if a Windows 7 client was updated to RDP v8 by installing Microsoft KB2592687, the same issue would be experienced if the LAN Manager authentication level is changed to anything other then the default.
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