Hi Andreas,

On Tue, May 24, 2011 at 10:40:41AM +0200, Andreas Kaiser wrote:
> Am 24.05.2011 um 09:57 schrieb Frank Heydlauf:
...
> > let's draw a chart (use monospaced font!):
> > 
> >                    ISP
> >                     |
> >                     |
> >                     |
> >                  4.3.2.17      
> >                   WAN
> >                  pfSense 
> >                 NAT+Filter
> >             LAN           OPT1
> >          1.2.3.1/26    1.2.3.129/25  
> >              |             |
> >              |             |                <-- VMware virtual switch
> >              |             |
> >          1.2.3.5       1.2.3.155  (for example)
> >            eth0        eth1
> >                Webserver
> > 
...
> > And the default-route of "Webserver" goes to 1.2.3.1 ?
> 
> Yes.

If you ping 1.2.3.155 from outside (ISP), the answer packets
will return via eth0 and 1.2.3.1.
At this point you may (probably will) hit anti-spoofing rules
and stateful filter rules at LAN interface.

=> You'll have to separate your answer-traffic on your
web-server based on rules, i.e. source routing based
on tcp source-port 443  or 80
or doing it in a more general way:
<http://kindlund.wordpress.com/2007/11/19/configuring-multiple-default-routes-in-linux/>

There are other options with NAT, proxies etc - but IMO none
of them better.

-- 
Gruss Frank

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