This may be due to the encryption type used by the rdp server.

On server 2003, under 'Administrative tools', select 'Terminal service
configuration'

Select the 'Connections' folder when the console appears, the on the
right hand pane select 'RDP-Tcp', right click and select 'Properties'

When the properties page appears, go to the 'General' tab and see what
option is set under 'Security layer'. 'SSL' does not work for me, but if
I set it to 'Negotiate' it does connect.

I can only assume that the rdesktop client knows nothing about ssl and
uses the standard rdp security (I have selected rdvpv5 and it still did
not work).

I recommend poking around the other tabs, you'll be able to set lots of
session option, most usefully under the 'Client Settings' tab.

Haven't tried this with Server 2k8, but I suppose it similar. Windows XP
does not seem to be configurable in this regard.

Cheers, 
Fish

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https://bugs.launchpad.net/bugs/181428

Title:
  Terminal Server Client Error

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