I know some of us use pfSense here and I’ve only used it for single-IP functions and for auto-sensing internet paths if a site doesn’t have a static address at the time of programming.

I’m moving away from single server design on my ESXi box to dedicated guests for each service but I cannot seem to get those dedicated services through the firewall.

I have a 29bit subnet (IPs 1 through 5). Everything is internal to the ESXi (5.1) server.

.1 = pfSense Firewall
.2 = OPT1 interface on pfSense
.3 = Customer VM (will port over to OPT2 after this works) 
.4 = All-in-one hosted VM
.5 = Same All-in-one hosted VM

I am going to eliminate .4 and .5 as I pull specific services out and into VMs (I’ve already moved the basic part of the FTP, the entire SQL server and LDAP to internal systems).

But whenever I set up NAT rules on .2 it seems to be using .1’s stuff.

I will have the following pushed through:
FTP
WWW (one primary, each subserver has functioning Apache for their services)
IMAP SSL/SMTP
SSH (via pushed ports to each server)

Any thoughts would be helpful. The biggest thing I need to get running now is the FTP part - I cannot get it to push through nor will it register on the firewall log that it’s being blocked.
—
Ryan