A. Jones wrote:
This is why I'm so confused...
There is no reason why it should not work.

Is there a way for me to see what the system is doing to the individual packets?
The scenario, exactly as you described, works for me very well without NAT-ing the public IP-s behind the firewall.

Do as Scott told you to do. Enable Advanced Oubound NAT rules and delete the one, used for your public network and/or add correct incoming rules on wan interface to accept the traffic.

On the other hand, you can always use this:

/usr/sbin/tcpdump -n -e -ttt -i pflog0

This will give you pretty clear idea, what's wrong.

/jan

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