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I have 3 NICS, one being a Wired network which connects to a wireless router, which is the primary network secured by WPA. Another being a Wireless USB Card I'm trying to setup to connect older machines with just WEP security, being able to disable when not needed. The 3rd being unused.

The first NIC is setup with IP Address Router The Wireless NIC is setup with IP Address

I have 2 DHCP Scopes, one for This being for NIC1, which gets DHCP requests The second is This is being for the Wireless NIC, which is not getting DHCP requests at all.

I Also have Routing and Remote Access enabled to try to tie the two subnets together as well as for VPN access, though I don't know how to set it up for LAN Routing purposes, only VPN purposes.

Running Windows Server 2003 R2.

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I think you might be encountering the same problem I did over in this question: Why would Windows Server not respond to DHCP DISCOVER?

You didn't mention the ranges you're using for your DHCP scopes, but I suspect that you're using a range which doesn't include the server's IP address. Try re-creating the scope with a larger range that includes your server's IP address, then use exclusion zones for any addresses that you don't want issued through DHCP.

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