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Scenario: We are looking at setting up a dedicated Windows Server (2008 R2) with a hardware firewall. The data center is recommending setting up rules to only allow certain IP Addresses through for things like Remote Desktop (RDP) and various other tasks. There are 4 individuals that will need routine access to the server, daily at first while things get setup. 2 developers work from home or on the road so their IP's changing daily (several times a day in some cases) so updating the firewall rules is not a good long term solution obviously, is it possible to setup a VPN connection to the server while still using the hardware firewall? If not, what are some options we can look into? Or, are there terms I can google to find this out - if so, please help me with terms and I'd be happy to google those terms myself.

The hardware firewall is requirement and the Windows Server OS has to be 2008 at this time.

UPDATE I found this article (https://www.geekyprojects.com/networking/how-to-setup-a-vpn-server-in-windows-server-2008-r2/) and others like it but no mention of a firewall device is ever mentioned. My thinking is though if the hardware doesn't even allow an unapproved IP through, then it doesn't matter if the server is configured to allow it through or not, right?

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  • If I understand your need correctly, you can certainly install a VPN server on the w2k8-r2 server, and depending on the kind of VPN you install then open the required ports on the firewall. If the VPN you choose has strong authentication (like certificates, for instance), then the firewall rule can be allowing connection from anywhere, and that would be reasonably secure. Another option, more elaborated and secure could be to install another dedicated machine, not so large, to act as a bastion host. That, for instance, will keep auditors much more happy.
    – Pablo
    Jun 20 '17 at 23:40
  • At this stage early of development, a second box isn't viable. On our first attempt with a dedicated server, about 24 hours after it was online, the box was being bombarded with login attempts, so many in fact that the server was useless to perform any other functions. DDOS attack, maybe? Once we got the hardware firewall in place, the server became usable again. Does that help?
    – HPWD
    Jun 21 '17 at 13:24
  • Pablo - I had to put this project on hold for the time being but back at it now. Are there free options for VPN (the bastion host scenario is not necessary, yet) or is this something our web host can setup? I'm just asking the questions they guy writing the check will want to know. :)
    – HPWD
    Jul 11 '17 at 15:15

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