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Is it possible to configure Windows Server 2008 to assign IP address to different subnets based on the Circuit Id and Remote Id using the DHCP server?

If so, how?

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Here is the same question answered for other DHCP server platforms:
DHCP on-the-fly block assignment

As far as Windows Server 2008, it looks like you will need to do some programming to get the behavior you want. You might want to check out the Microsoft Windows DHCP Team Blog here:

http://blogs.technet.com/b/teamdhcp/

These blog entries seem to cover parts of what you want to do:
Option based IP Address assignment Callout Dll
DHCP Server Callout API usage

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