Desktop windows manager has stopped working

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An interesting side note is that I can have him remote log in to the server from another computer without any issues. I'm not sure what to do about all of this. Check the status of the Remote Desktop Device Redirector in the System folder of Device Manager. Redirected printing will no longer function for a single user session. The 1103 error states: An internal communication error occurred. Ensure that the computer account for the license server is a member of Terminal Server License Servers group in Active Directory domain 'DOMAIN'. The 4105 states: The Remote Desktop license server cannot update the license attributes for user 'USER' in the Active Directory Domain 'DOMAIN'. I looked through the event log on the server and found a 4105 and several 1103 errors each time he tried to connect. He will connect for a few seconds without issue, then Remote Desktop crashes and offers to send a report to Microsoft. One of our users who used to be able to log in from his Win7 to Win2008 server can't anymore. So I've run into a tricky problem I can't figure out.