J. Ryan Earl wrote:
Turns out, all the setsockopt may have had nothing to do with the problem. That should have only been a problem if I was using IPSec Pass Thru, ie setting up a VPN from inside of a NAT to an end-point outside the NAT.

So here's the real problem as far as I can tell. pfSense only supports IPSec tunnels that originate from the "WAN" interface on the pfSense firewall. I have 2 ISP connections:
 WAN => T1 (209.198.142.210)
 OPT1 => DSL (216.62.203.233)
ipsec tunnel off of OPT1 works fine here.




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