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I have a new Windows Server 2008 R2 machine that I have setup. All file shares are setup and working well on our internal network. However, when we VPN in from an outside address (via our Astaro Firewall - SSL VPN), we are unable to access this server.

I am not able to ping the server from the outside either but it does respond to ping internally. I have 2 other Windows Server 2008 R2 machines, all Standard Edition, running and they work fine via the VPN. I've compared all Firewall rules and everything is the same across all 3 machines. The other 2 machines can be pinged from the VPN network as well.

Would this lead you to believe I'm still missing something from the server level or something blocking the traffic in the VPN? BTW: I'm pinging the server by IP address and not name. I'm not counting on or expecting DNS to traverse the VPN as it is not setup to do so.

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Are all three servers on the same subnet? Are the IP gateway & subnet mask the same on all servers? – uSlackr Jun 12 '12 at 17:08
Did you try disabling the firewall on that server and running a test again? – Vick Vega Jun 12 '12 at 17:09
Yes - same subnet. Disabling firewall doesn't seem to make any difference. – Jeff Jun 12 '12 at 17:17

Resolved. Found that the Subnet Mask on the machine not responding via VPN was set to instead of Whoops! /16 Network.

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