vSphere.

Create an "Alias" and use it as "Source" ;) https://doc.pfsense.org/index.php/Aliases A Reading at the Doc's wouldn't hurt you :P https://doc.pfsense.org/index.php/Main_Page

You could put pfsense in a bridge with filtering turned off and some of the packages mentioned in the link. I am not sure if they work on the bridge interface or LAN/WAN or if at all. But it is worth a shot.

A transparent proxy is invisible for all intents and purposes to the client You could log all traffic, but when it is encrypted you will just see a garbled mess You will not be able to see encrypted traffic without modifying the clients

A 1gb port can do 1gb both ways, which is 2gb/s.

http://www.newegg.com/Product/Product.aspx?Item=N82E16833704011 These are the cards I put in

@stephenw10: Good to know. Did this start happening immediately when you installed the Squid3 package then or maybe after some package update. You could use the Squid2 package instead, that is supported by the devs and this sort of issue would be a show stopper. Steve no.. i think it takes at least 1 month or 2 after squid installation. atm we use handycafe filter to block porn sites, etc. so pfsense handles only for policy routing, firewall, ntp server, dhcp server

That's great advice.  I'll see if I can get  capture during an outage. Jeff

Thanks for your answer. The main problem is that i want to recieve the notification form the pfSense firewall itself (under System -> Advanced -> Noticfication) so there is no interface that the traffic enter. Of course i could change my VPN Tunnel that it is not the default Gateway, but i hope there is another way. //EDIT My VPN Priovider whitelisted my needed SMTP Servers… It works  - done!