Thank you for the response, I do appreciate the assistance.
Here is what i have discovered, location A and B are connected via ipsec. Location A holds the mail server. Location B is unable to ping Location A's External Ip. Location A is unable to ping location B's external Ip
Location B can ping Locations A's INTERNAL IP
After looking through the logs I was able to allow Location a to ping Location B, I had to enable ICM (echo request).
Unfortunately reversing this on location B was unsuccessful.
I have used traceroute for (mail@mydomain.com) which points to location A's external IP on the remote network
the route is incomplete at ip 64.230.152.250
I then ran a traceroute at 64.230.152.250
the route gave one hop from my pfbox to 50.43.250.1 then the hop became incomplete.
I installed Microsoft Network monitor on a server in Location B and filtered 50.43.250.1
This was the result
943021 2:01:37 PM 3/19/2013 12161.0588449 System PRISMUSASERVER 50.43.250.1 NbtNs NbtNs:Query Request for *<00><00><00><00><00><00><00><00><00><00><00><00><00><00><00> <0x00> Workstation Service {UDP:7589, IPv4:7513}
943023 2:01:37 PM 3/19/2013 12161.0744699 50.43.250.1 PRISMUSASERVER ICMP ICMP:Destination Unreachable Message, Port Unreachable, 50.43.250.1:137 {IPv4:7513}
943095 2:01:39 PM 3/19/2013 12162.5588449 System PRISMUSASERVER 50.43.250.1 NbtNs NbtNs:Query Request for *<00><00><00><00><00><00><00><00><00><00><00><00><00><00><00> <0x00> Workstation Service {UDP:7589, IPv4:7513}
943099 2:01:39 PM 3/19/2013 12162.5744699 50.43.250.1 PRISMUSASERVER ICMP ICMP:Destination Unreachable Message, Port Unreachable, 50.43.250.1:137 {IPv4:7513}
945442 2:02:49 PM 3/19/2013 12232.6994699 50.43.250.1 PRISMUSASERVER ICMP ICMP:Time Exceeded Message {IPv4:7513}
945444 2:02:49 PM 3/19/2013 12232.7307199 50.43.250.1 PRISMUSASERVER ICMP ICMP:Time Exceeded Message {IPv4:7513}
945446 2:02:49 PM 3/19/2013 12232.7463449 50.43.250.1 PRISMUSASERVER ICMP ICMP:Time Exceeded Message {IPv4:7513}
945527 2:02:53 PM 3/19/2013 12237.1994699 System PRISMUSASERVER 50.43.250.1 NbtNs NbtNs:Query Request for *<00><00><00><00><00><00><00><00><00><00><00><00><00><00><00> <0x00> Workstation Service {UDP:7589, IPv4:7513}
945528 2:02:53 PM 3/19/2013 12237.2150949 50.43.250.1 PRISMUSASERVER ICMP ICMP:Destination Unreachable Message, Port Unreachable, 50.43.250.1:137 {IPv4:7513}
945566 2:02:55 PM 3/19/2013 12238.6994699 System PRISMUSASERVER 50.43.250.1 NbtNs NbtNs:Query Request for *<00><00><00><00><00><00><00><00><00><00><00><00><00><00><00> <0x00> Workstation Service {UDP:7589, IPv4:7513}
945568 2:02:55 PM 3/19/2013 12238.7150949 50.43.250.1 PRISMUSASERVER ICMP ICMP:Destination Unreachable Message, Port Unreachable, 50.43.250.1:137 {IPv4:7513}
945626 2:02:56 PM 3/19/2013 12240.1994699 System PRISMUSASERVER 50.43.250.1 NbtNs NbtNs:Query Request for *<00><00><00><00><00><00><00><00><00><00><00><00><00><00><00> <0x00> Workstation Service {UDP:7589, IPv4:7513}
945629 2:02:56 PM 3/19/2013 12240.2150949 50.43.250.1 PRISMUSASERVER ICMP ICMP:Destination Unreachable Message, Port Unreachable, 50.43.250.1:137 {IPv4:7513}
looking through location A logs I see no records of Location B's ext Ip, or 50.43.250.1
As for DNS forwarding, My domain has a DNS server, (windows) I assume I would need to put this into the DNS server instead of the PFbox I can't seem to get this to work either.
Any more ideas would be appreciated. I have tried to use the DNS forwarding via pfsense (location b) but also unsuccessful, I'm going to reboot the firewall tonight when no one is online, With hopes that there mayu be a glitch although I doubt there is.
"Do such pings go over the public internet or over the VPN? On which path should they go? Why?"
I expect the pings go outside the VPN, which is ok, this will allow my laptop users which fluctuate inside and outside the building to use the same setting.