I have a Windows 7 Enterprise vm running Cisco VPN Client I'm connected to this Windows box via RDP. I have a Linux server that needs to route through the VPN on this Windows server. Attempts to use vpnc to connect to the VPN server on the Linux box have resulted in "vpnc: no response from target". The Linux box can reach the VPN server via nmap on ports 500 and 4500, so we know the issue is not with the network but vpnc. The windows vm is in the same subnet as the Linux box. I can reach the windows box via the linux server and my workstation.

However, when I start the VPN connection, RDP gets disconnected. Windows firewall is completely disabled, transparent tunneling is enabled in the VPN client (IPSec over UDP) and "Allow Local LAN Access" is enabled. When I load the virtualization console for the Windows vm, I can confirm that it now has access to the VPN.

What appears to be happening is that the Cisco VPN client is not honoring the "Allow Local LAN Access" setting, as far as I can tell.

Is this a known bug perhaps? Anyone have experiencing routing through a windows machine in order to use the Cisco VPN client?


A couple steps to try troubleshooting:

Can you use the VPN from any Windows clients on the network? (or any other clients on the LAN for that matter; anything the hosting VM. If understand your post correctly this device is the only one that can connect over the VPN.)

When trying to connect to the VPN VM [from the linux server] run the following command on the server to see if the network connection is building: netstat | find /N "x.x.x.x" //where x.x.x.x is the Linux server IP

This will tell you if the network connection is building. (You can actually watch the SYN-ACK handshake build.) Just because you can connect at 500 and 4500 doesn't mean that other needed ports may be working (ie: 10000 [UDP], 50, 51 [IP]).

P.S. Cisco AnyConnect rewrites the hosts route tables when activated to specifically prevent split tunneling (to prevent the tunnel from being bypassed). This would require taskmanager or a batch file to restore the internal routes after the VPN is established.

  • If you would rater skip troubleshooting and just double check your configs the cisco documentation to configure aCisco VPN client can be found here. It may seems tedious but check each step as the most common reason a VPN fails is an accidental misconfiguration. cisco.com/c/en/us/support/docs/security/… – TechMonk Jul 19 '16 at 21:26

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