Win7 to W2K8 R2 Remote Desktop fails, yet 3rd party Remote Desktop client connects ok

network-level-authremote desktop

Without any change (except Windows Updates), one of my stand alone W2K8 R2 servers has become unconnectable from Remote Desktop (Win 7). RDP gets stuck on 'Securing Remote Connection' and just never completes.

I can however connect to the same server using a 3rd party RDP client – Royal TS – which allows me to specifically disable Network Level Authentication. Connecting with NLA enabled in Royal TS exhibits the same problem as Win7 RDP client.

The W2K8 R2 server is configured to allow non NLA RDP sessions. Not a member of a domain, not a DNS server, etc. It's a standalone web server.

So, my question is what could cause RDP to fail like this with no other changes?

UPDATE
In a bizarre twist, the problem has magically resolved itself with no changes on either end.

I have a suspicion there may have been some kind of DNS issue within the hosting center – based on comments I've found through google from others experiencing similar kinds of problems.

Best Answer

Is it possible that your Win 7 box got the RDP 6.1 update? If so, perhaps it is failing server authentication. Did you try from another client such as an XP box?

Here's what I'm referring to:

http://support.microsoft.com/kb/951616

Server authentication
In RDC 6.1, server authentication verifies that you are connecting to the correct remote computer or remote server. This security feature helps prevent you from connecting to a computer or server to which you did not intend to connect. This feature also prevents you from unintentionally exposing confidential information.

By default, server authentication is enabled for the connection. However, if you want to change server authentication settings, follow these steps:

    Click Start, click All Programs, click Accessories, click Communication, and then click Remote Desktop Connection.
    Click Options, and then click the Advanced tab. 

The three available authentication options are as follows:

    Always connect, even if authentication fails
    If you enable this option, you can connect even if RDC 6.1 cannot verify the identity of the remote computer.
    Warn me if authentication fails
    If you enable this option, RDC 6.1 tells you if it cannot verify the identity of the remote computer. This option gives you the choice of whether to continue with the connection.
    Do not connect if authentication fails
    If you enable this option, you cannot connect if RDC 6.1 cannot verify the identity of the remote computer.
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