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


  • 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!

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  • Barring any firewall changes, I would reboot your firewall and/or router. – joeqwerty Jul 15 '11 at 20:26
  • Hi joeqwerty, No firewall changes in Windows Server, or the router. Already reboot router and server itself. – Caffeinated Aviator Jul 15 '11 at 20:30

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

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  • What happens when you telnet to the RDP port from outside your network? – user48838 Jul 16 '11 at 2:01
  • Good call. Telnet seems to indicate it is getting through (no connect failed message or anything like that). – Caffeinated Aviator Jul 17 '11 at 4:03
  • But what is actually being displayed? – user48838 Jul 17 '11 at 17:09
  • Your standard blinking cursor – Caffeinated Aviator Jul 17 '11 at 17:26
  • Then something else is probably intercepting the ssh session, you might compare it to a session from within your network. – user48838 Jul 17 '11 at 17:36

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