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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.
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Only option to get same session ID for user is to configure \ restrict users to a single session on terminal server and the user must leaves the session in a disconnected state, so that user will automatically reconnect to that session only next time when connected.
Check below article to enable single session restriction through Terminal server itself or through GPO
http://technet.microsoft.com/en-us/library/cc754762.aspx
Only you need to increase timeout for disconnected sessions, otherwise if session get disconnected, it will create new session with new session ID
I hope this is the setting you are looking for. Correct me if wrong please
Mahesh