VPN and Remote Desktop Stopped Working (Windows Server 2008 R2)

remote desktopremote-desktop-servicesvpnwindows-server-2008windows-server-2008-r2

Recently, both the VPN and remote desktop stopped working. See below for details.

VPN:

  • Error 800: The remote connection was not made because the attempted VPN tunnels failed. The VPN server might be unreachable. If this connection is attempting to use an...

Remote Desktop:

  • Still accessible from within LAN
  • Gets stuck on Configuring remote session... from outside the network

From what I've gathered, every other service is working perfectly. All ports appear to be forwarding properly, and I can access the various web interfaces that are served via that server. This issue seems to be centered around the VPN and remote desktop feature. I have tried restarting different services, and did a physical reboot.

Any ideas, links, etc., would be greatly appreciated. Thanks in advance!

EDIT: The Remote Desktop functionality works when VPN is disabled. The utter randomness of this is frustrating!

Best Answer

You might check to see if any recent firewall changes have taken place.