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I have a Windows 2008 RRAS server with 4 external IP's. Is it possible within RRAS to send outbound traffic through each external IP address once I'm connected to the VPN on that specific IP address? That is to say, I connect to via VPN, and I want my traffic from that VPN to go back externally through

Every time I try it now it defaults to one specific public IP address even though I'm successfully connecting on a different one.

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I don't think that functionality is native to RRAS. You're probably going to need to look into either a hardware firewall that can do that, or the Forefront Threat Management Gateway (or, in plain English, MS's overblown name for a server software firewall).

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