What you're sewing is the proxy doing what you've told it to do. When the pc on 
the lan side (any vlan) requests a connection to a server the proxy makes that 
request on its behalf and returns the packets sent back from that request.  In 
order for that to happen on a secured connection the proxy must set up a secure 
connection to he remote server (or in your case other interface server) as well 
as a separate secure connection between the proxy and the originating client 
pc. Doing it any other way requires either passing the traffic directly through 
the firewall or breaking the secure connection.  This is one of the 
consequences of doing NAT. I'm guessing the main complaint is that the firewall 
cert isn't trusted and triggers browsers. 

<div>-------- Original message --------</div><div>From: Ryan Clough 
<ryan.clo...@dsic.com> </div><div>Date:12/12/2014  13:58  (GMT-05:00) 
</div><div>To: pfSense Support and Discussion Mailing List 
<list@lists.pfsense.org> </div><div>Subject: Re: [pfSense] Traffic routing 
issue </div><div>
</div>>Oliver,
>
>
>I apologize, I should have been more clear. The problem is exhibited from all 
>VLANs if I force the use of the web server's public IP. I only just discovered 
>it while testing the guest WiFi on the restricted VLAN.
>
>
>To answer your questions:
>
>The pfSense router is not aware of any VLANs, we use a layer 3 switch that 
>sits just inside from the pfSense router that routes traffic that must exit 
>the LAN to the pfSense router.
>
>
>I have attached screen shots of my port forward rule and the auto-generated 
>firewall rule.
>
>
>Thank you very much for your help.
>
>
>
>
>Ryan Clough
>Information Systems
>Decision Sciences International Corporation
>
>
> 
>On Fri, Dec 12, 2014 at 9:15 AM, Oliver Hansen <oliver.han...@gmail.com> 
>wrote:What does the allow rule on the restricted vlan and the NAT rule look 
>like? 
> On Dec 11, 2014 11:24 PM, &quot;Ryan Clough&quot; <ryan.clo...@dsic.com> 
> wrote:
>
>
>I am hoping that one of you out there can assist me with this rather 
>interesting problem I am having. Let me set the stage.
>
>
>I am running the latest stable version of pfSense:
>2.1.5-RELEASE (amd64)
>built on Mon Aug 25 07:44:45 EDT 2014
>FreeBSD 8.3-RELEASE-p16
>
>I am running transparent Squid and Squidguard, and all IP ranges have access 
>to use the proxy.
>
>
>I have two WAN connections, each with a handful of public IPs. I have created 
>an IP alias virtual IP of one of my public IPs on WAN1, which is used to NAT 
>to a web server.
>
>
>We have an internal DNS server that resolves the domain name of a web server 
>to the local LAN IP address. So, all computers on unrestricted VLANs access 
>the web server without having to hit the pfSense router at all. This works as 
>expected and the valid certificate is served and the web page loads.
>
>
>We have one restricted VLAN that is used for guest WiFi access and this VLAN 
>is assigned external DNS servers and therefore resolve the domain name to the 
>public IP.
>
>
>
>Now my problem. When connected to the guest WiFi on the restricted VLAN and 
>attempting to access the web server on its public IP, which is assigned to a 
>virtual IP on WAN1, I get served the certificate from the pfSense router. I 
>can tell that this is the pfSense self-signed certificate because of the 
>details of the certificate displayed in the warning. I also get this behavior 
>if I force a computer on an unrestricted VLAN, using the hosts file, to 
>resolve the host name of the web server to its public IP.
>
>
>What is going on here? I can provide more information if needed. Thank you for 
>your time.
>
>Ryan Clough
>Information Systems
>Decision Sciences International Corporation
>
>
> 
>
>
>
>
>
>
>
>
>
>
> 
> 
>
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