It's easy to figure out how to do this but this has always been one of those "Windows Server 2008 R1" default settings that drives me crazy after I complete a clean install of the server OS. I'm not sure if this has changed in R2 but for those looking for quick instructions on how to enable multiple RDP sessions to Windows 2008 Server R1, complete the following items:
1. GPedit.msc
2. Computer Configuration
3. Administrative Template
4. Windows Components
5. Remote Desktop Services
6. Remote Desktop Session Host
7. Connections
8. Restrict Remote Desktop Service users to a single Remote Desktop Services session
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