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I recently purchased a cloud server to use for backup. This server is configured with public IP address, and has Windows Server 2016 installed on it.

On the other hand, I have a Windows Server 2008 behind a firewall, and the local area network.

My intention is to create a mapped drive on the remote server (cloud server) and deploy it by group policy (from windows server 2008) so that the users can backup their files to their own cloud directory.

I already installed and successfully configured Routing and Remote Access role on the cloud server, I tested connecting to it from a dial-up connection on one of my machines on the LAN. This is working fine. Now what I need is to map this folder using Group Policy on the LAN from windows server 2008, so that the drive is showing without them needing to connect to the dial-up connection prior to login. Is that possible somehow?

Thank you in advance for your assistance.

  • I recently purchased a cloud server to use for backup - How about giving us specifics about this server? Is it an AWS EC2 instance? Is it an Azure instance? What exactly is this "cloud server"? – joeqwerty May 11 '17 at 15:56
  • @joeqwerty, it is a dedicated private server – Hani El Mouallem May 12 '17 at 7:54
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Do not use RRAS VPN for this: it is still an obsolete PPTP VPN with all its vulnerabilities.

Method A: For a cloud located server used for internal purposes I'd choose a solution where the server hasn't got external network at all. For example, Microsoft Azure has Virtual Networks where your server can be connected only through a site-to-site VPN.

Method B: Now that you probably already have a contract with a cloud provider that doesn't necessarily have such possibilities, you could install an OpenVPN Server to your Windows Server 2016 in cloud and use your firewall / router as an OpenVPN client, enabling your whole network to connect to the server at once – just like it was on your local network.

After you have your VPN set up with either of the methods described above, you can map your network drives with Group Policy exactly the same way you do it with your local server.

  • I will give it a shot now and let you know the outcome once implemented. – Hani El Mouallem May 12 '17 at 7:56
  • This can't be accomplished, my firewall cannot connect to OpenVPN as client. – Hani El Mouallem May 15 '17 at 7:15

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