I have posted this to NetworkEngineering.SE, as that seems the more suitable audience for this question.

I will leave this question open here but am happy to see it closed. I just did not want to delete it in case someone was working on a reply.

I am running pfSense 2.1 and having an issue with a Proxy.sh setup. In particular, I have pfSense configured to connect over OpenVPN to the Proxy.sh server us-nj.proxy.sh and to infinitely resolve the server.

It seems that the servers change from time-to-time, so pfSense has to re-resolve us-nj.proxy.sh. Unfortunately the system tries to connect to DNS (Google's and through the now-disconnected proxy.

The server has interfaces WAN (being to my ISP, named WAN_DHCP) and OPT1 (being to the Internet via the OpenVPN interface, named ProxySHGW)

I have configured the pfSense outbound NAT as follows:

Interface  Network   Protocol     WAN/OPT1     Ports 
WAN      any      tcp/udp/53     WAN     *       Straight DNS   
WAN  tcp/993     WAN     *       SMTP NAT   
WAN  tcp/*   tcp/465     WAN     *       SMTP/S NAT     
OPT1    *   OPT1    *       LAN to OPT1    
WAN      *   WAN     *       LAN to WAN     
WAN         *   WAN     1024:65535      localhost to WAN   
OPT1         *   OPT1    1024:65535      localhost to OPT1 

As you can tell the network is split, with IP addresses – 255 going to the OPT1/OpenVPN, and – 127 to the WAN.

The firewall rules are as follows:

Proto Source  Port  Destination Port  Gateway
IPv4 *     *   *   *   WAN_DHCP
IPv4 *     *   *   *   WAN_DHCP 
IPv4 TCP   LAN net   *   *   465 (SMTP/S)  WAN_DHCP 
IPv4 TCP   LAN net   *   *   993 (IMAP/S)  WAN_DHCP 
IPv4 *  *   *   *   ProxySHGW
IPv4 *  *   *   *   WAN_DHCP

I would think that these firewall and NAT would cause DNS requests to route over the WAN, but in practice it does not.

Strangely enough though the SMTP/S and IMAP/s routing does work as expected.

Any thoughts on what might be going on here would be much appreciated.

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