FAQ cisco vpn pass thru not working when behind pfSense

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Summary

If you are having trouble getting an internal Cisco VPN client to connect to an external host, (e.g. a workstation with the Cisco client is trying to get out through pfSense to connect to a "foreign" site), then try the following.

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Workaround

  • In the Cisco VPN client software, Modify the connection and turn off transparent tunneling completely in the Transport tab.
  • In the pfSense, under Firewall -> NAT -> Outbound, enable Advanced Outbound NAT. (If you have a multi-WAN configuration be sure to copy the auto-created rule for the other interfaces as well).
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