I have a Windows 2008 server setup in the cloud as a RRAS running VPN access and NAT. It is joined to a domain controller also running in the cloud. A Windows 7 VPN client connects using SSTP to the RRAS server and everything works except for connectivity to the RRAS server itself. That is, the client can ping/ftp/etc other remote servers via the VPN, and they can ping the client, but operations like file copy done between the RRAS server and the VPN client fail intermittently or are very slow. The client is not running split tunneling.

For example, copying a 1 MB file to or from the server will typically work, but copying a 100 MB file rarely will finish successfully. Copying the same 100 MB file to or from a different remote server via the VPN works fine.

The client can also ping the RRAS server on all of its IP addresses (both private and public sides of the NAT).

To summarize, the client can access the remote network fine via the RRAS VPN gateway, but has networking issues with the RRAS gateway server itself. I'm not sure at this point where to even begin in troubleshooting this. Any ideas?

  • is your windows 7 machine trying to connect using IPv6? perhaps you need to allow that through your firewall – Brian Sep 15 '11 at 4:10
  • @Brian: Thanks for the suggestion, but I disabled IPv6 for the client's connection settings so I don't think that's the issue. Also, I have tried this with the firewall disabled. – emfurry Sep 19 '11 at 16:34
  • @emfurry, did you get the bottom of this? I have a v.similar issue with Windows 7 -> Windows Server 2008 via a VPN. – Mike Q Jan 15 '12 at 18:34

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