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Cannot Connect to Windows 2008/R2 Remote Desktop Services from Windows 2000

NB. This article is intended for a highly technical audience.

When attempting to connect to a Remote Desktop Services server running Windows 2008/R2, a Windows 2000 client reports: “Because of a security error, the client could not connect to the remote computer. Verify that you are logged on to the network, and then try connecting again.”

This occurs only when Remote Desktop Client Access Licences have been installed on the server. The problem does not occur if the server is running Remote Desktop Services for Administration use only. The issue is that the certificates used by the Remote Desktop Licencing Server when the server has been automatically activated are not compatible with the Remote Desktop client used on Windows 2000 (RDP 5.0).

To resolve:

  1. In Remote Desktop Licencing Manager, go to All Servers → <Server> and deactivate the server.

  2. Then go to All Servers → <Server> → PropertiesConnection Method and set Connection Method to Web Browser.

  3. In Registry Editor, navigate to HKEY_LOCAL_MACHINE\SYSTEM\CurrentControlSet\Control\Terminal Server\RCM and delete the following keys:

    Certificate

    X509 Certificate

    X509 Certificate ID

    X509 Certificate2

  4. Restart the following services: Remote Desktop Services and Remote Desktop Licensing.

  5. Open Remote Desktop Licencing Manager and reactivate the server using the Web Browser method.

If this does not resolve the problem, repeat but instead of using the Web Browser method, use the Telephone method to activate the server.

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