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Please recreate the user and try it again.<br />
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If not working then removed from AD and join again if AD in picture.
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Please recreate the user and try it again.

If not working then removed from AD and join again if AD in picture.

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ummm, this has nothing to do with AD. &nbsp;This is a thin client not on the domain at all.
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ummm, this has nothing to do with AD.  This is a thin client not on the domain at all.

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Pulling straws here...<br />
<br />
Is Network Level Authentication set for XP? <a href="https://ingazat.wordpress.com/2010/02/12/enabling-nla-on-windows-xp-for-win-2008-terminal-services/" rel="ugc">https://ingazat.wordpress.com/2010/02/12/enabling-nla-on-windows-xp-for-win-2008-terminal-services/</a><br />
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Or maybe saving settings to a .rdp file: <a href="http://www.edugeek.net/forums/thin-client-virtual-machines/62950-windows-2008-r2-remote-desktop-double-login.html#post566083" rel="ugc">http://www.edugeek.net/forums/thin-client-virtual-machines/62950-windows-2008-r2-remote-desktop-double-login.html#post566083</a>
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Pulling straws here...

Is Network Level Authentication set for XP? https://ingazat.wordpress.com/2010/02/12/enabling-nla-on-windows-xp-for-win-2008-terminal-services/ [https://ingazat.wordpress.com/2010/02/12/enabling-nla-on-windows-xp-for-win-2008-terminal-services/]

Or maybe saving settings to a .rdp file: http://www.edugeek.net/forums/thin-client-virtual-machines/62950-windows-2008-r2-remote-desktop-double-login.html#post566083 [http://www.edugeek.net/forums/thin-client-virtual-machines/62950-windows-2008-r2-remote-desktop-double-login.html#post566083]

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Found own solution. &nbsp;Thanks!
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I have an XP thin client connecting to a 2008 R2 server. &nbsp;It is requiring the people to enter their credentials twice. &nbsp;Once for the RD gateway and once for the RD server. &nbsp;This did not happen on their old 2003 box so something security wise changed. &nbsp;I have the check box for use credentials for RD gateway checked, but that doesn't seem to be working. &nbsp;Any ideas?
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I have an XP thin client connecting to a 2008 R2 server.  It is requiring the people to enter their credentials twice.  Once for the RD gateway and once for the RD server.  This did not happen on their old 2003 box so something security wise changed.  I have the check box for use credentials for RD gateway checked, but that doesn't seem to be working.  Any ideas?

XP rdp session requires double login

Windows Server 2008 and Windows Server 2008 R2, based on the Microsoft Vista codebase, is the last 32-bit server operating system released by Microsoft. It has a number of versions, including including Foundation, Standard, Enterprise, Datacenter, Web, HPC Server, Itanium and Storage; new features included server core installation and Hyper-V.