Well, I got it working!

I couldn't get it to forward specific traffic (port 25) through the IP address, 
but I'll still keep trying. This is my intended goal.
I had a block of IP's on a /29 subnet issued by the ISP, which was on a 
different subnet than the assigned single IP which was on a /24 from the ISP.
I also changed all virtual IP's to OTHER and not IP Alias since they were on a 
different subnet.

Here's what I did to get all traffic from a specific internal IP to flow to a 
virtual IP as a default gateway:

Do not NAT - disabled / unchecked
Interface - WAN
Source - IP of internal LAN server to go out x.x.x.x/32 since I only want a 
single IP - EVEN if it is on a /24 internally.
Destination - blank (ANY)
Translation - Address: My Virtual IP assigned with the proper SUBNET - in my 
case /29.
Static Port Yes
Before creating the rule, on the rule page select: Manual Outbound NAT rule 
generation (AON - Advanced Outbound NAT)

I did nothing but set security in my vSwitch to promiscuous. That was set prior 
to this post.

From: [email protected] [mailto:[email protected]] On 
Behalf Of Marc R. Meshurle Jr.
Sent: Monday, April 15, 2013 00:00
To: pfSense support and discussion
Subject: Re: [pfSense] Virtual IP's and outbound NAT

Promiscuous Mode is set in the security options on the WAN NIC which is 
established in the vSwitch. What other settings need to be set?

Subject: Re: [pfSense] Virtual IP's and outbound NAT

>I have a PFS 2.02 running nicely on VMware 5.1. IT has only TWO NIC's 
>assigned. WAN NIC on the PFS is set to accept promiscuous traffic.
>I have a block of 6 IP's that I have set up as virtual IP's in PFS. I've read 
>every blog, post and news item that I can find to force specific outbound 
>traffic through one NIC and can't get it to >work.

You need to make changes on the vSwitch for this to work. Check the options 
that you have set on the attached vSwitch on the security tab of the vSwitch 
properties.

Dimitri Rodis
Integrita Systems LLC
http://www.integritasystems.com

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