I have servers in one location that need to access servers in another location. The only connection between them is the Internet but it's 100Mbs and only has about 4 hops.

At the moment to access the remote server we run a local proxy server with one NIC on the local LAN and the other NIC connected to a business router/firewall.

A user on the local LAN can use something like tunnelier to SFTP to the remote server (both are Windows Server 2008) and then tunnel RDP through SFTP. That works pretty well so we can access the remote server and perform file transfer.

However we would like the remote server if possible to join the local Domain. The first thought was to use a site to site VPN using Windows Server on both machines to enable this. That would presumbly be a L2PT VPN.

But our hosting provider has suggested we use a IPSEC VPN with the connections being done at the router level.  That makes sense since it means we don't have to mess with Server configurations but I am wondering how it would work.

For protocols that are well defined like http, https, sftp, it is easier enough to tell the source application (browser, sftp program) to use the proxy server. But something like RDP where you cannot tell it to use the proxy server would the Internet settings in Windows be enough to provide access to the remote server across the VPN?

And finally if you wanted to do Windows file sharing so that you could browse shares on the remote server, it's not clear how to do that.

Any pointers would be appreciated.

By the way if there is a Microsoft network engineer reading this and lives in Wellington and would be keen on some short term consulting work to help me, drop me a PM.

Thanks