Using Cisco VPN Pass Through Behind pfSense

If trouble is encountered when attempting a connection from an internal Cisco VPN client to an external host, (e.g. a workstation with the Cisco client is trying to get out through a pfSense® firewall to connect to a “foreign” site), then try the following.

Workaround

• In the Cisco VPN client software, Modify the connection and turn off transparent tunneling completely in the Transport tab.

• In the pfSense webGUI, under Firewall > NAT on the Outbound tab:

  • Enable Manual Outbound NAT.

  • Remove any NAT rules that perform static port NAT on udp/500.