Exch 2007 and IIS SMTP behind Firewall, bouncing internal emails   

We have an Exchange 2007 Server AND a separate IIS SMTP Server behind
a pfSense Firewall.

We do a lot of outbound emails (Mass Emails, Confirmation, etc...) and
for some logistics reasons (eg. don't want to bother our Exchange when
we need to send 20,000 notifications to our members), we want to keep
the Exchange Server handling email and the IIS/SMTP server dedicated
to these automated/Mass Email type messages.

We have a partial Class C net, each server has their own dedicated IP
(Public and Private). Port 25 rules for the firewall.

We are running into a problem when a automated email is sent to an
internal email address (meaning, it direct to our exchange server from
our IIS/SMTP server). The message is from ourselves and to ourselves
(eg. from doug@domain.com to steve@domain.com but using IIS/SMTP
instead of exchange). We get an error message like this...

Delivery has failed to these recipients or distribution lists:

doug@domain.com
Your message wasn't delivered because of security policies. Microsoft
Exchange will not try to redeliver this message for you. Please
provide the following diagnostic text to your system administrator.


Diagnostic information for administrators:

Generating server: smtp1.domain.com

doug@domain.com
#< #5.7.1 smtp;550 5.7.1 Message rejected as spam by Content
Filtering.> #SMTP#

Original message headers:

Received: from web1 ([10.10.10.253]) by smtp1.domain.com with
Microsoft
 SMTPSVC(6.0.3790.3959);	 Tue, 5 Feb 2008 18:25:07 -0500
MIME-Version: 1.0
From: 
To: 
Date: Tue, 5 Feb 2008 18:25:08 -0500
Subject: Test Subject
Content-Type: text/html; charset="us-ascii"
Content-Transfer-Encoding: quoted-printable
Return-Path: DoNotReply@domain.com
Message-ID: 
X-OriginalArrivalTime: 05 Feb 2008 23:25:07.0715 (UTC)
FILETIME=[583C6530:01C8684E]

Any ideas on how to get this working?

date: Tue, 5 Feb 2008 15:40:00 -0800 (PST)   author:   unknown

Re: Exch 2007 and IIS SMTP behind Firewall, bouncing internal emails   

Add the IP address of the IIS server to the internal SMTP servers list

 Telling Exchange about (non-Exchange) SMTP servers
http://exchangepedia.com/blog/2006/08/telling-exchange-about-non-exchange.html

 Exchange Server 2007: Making SenderID work with non-Exchange smtp hosts
http://exchangepedia.com/blog/2007/01/exchange-server-2007-making-senderid.html

-- 
Bharat Suneja
MVP - Exchange
www.zenprise.com
NEW blog location:
exchangepedia.com/blog
----------------------------



 wrote in message 
news:042a834b-4e25-44d2-a693-6ce9ef4db1f1@i7g2000prf.googlegroups.com...
> We have an Exchange 2007 Server AND a separate IIS SMTP Server behind
> a pfSense Firewall.
>
> We do a lot of outbound emails (Mass Emails, Confirmation, etc...) and
> for some logistics reasons (eg. don't want to bother our Exchange when
> we need to send 20,000 notifications to our members), we want to keep
> the Exchange Server handling email and the IIS/SMTP server dedicated
> to these automated/Mass Email type messages.
>
> We have a partial Class C net, each server has their own dedicated IP
> (Public and Private). Port 25 rules for the firewall.
>
> We are running into a problem when a automated email is sent to an
> internal email address (meaning, it direct to our exchange server from
> our IIS/SMTP server). The message is from ourselves and to ourselves
> (eg. from doug@domain.com to steve@domain.com but using IIS/SMTP
> instead of exchange). We get an error message like this...
>
> Delivery has failed to these recipients or distribution lists:
>
> doug@domain.com
> Your message wasn't delivered because of security policies. Microsoft
> Exchange will not try to redeliver this message for you. Please
> provide the following diagnostic text to your system administrator.
>
>
> Diagnostic information for administrators:
>
> Generating server: smtp1.domain.com
>
> doug@domain.com
> #< #5.7.1 smtp;550 5.7.1 Message rejected as spam by Content
> Filtering.> #SMTP#
>
> Original message headers:
>
> Received: from web1 ([10.10.10.253]) by smtp1.domain.com with
> Microsoft
> SMTPSVC(6.0.3790.3959); Tue, 5 Feb 2008 18:25:07 -0500
> MIME-Version: 1.0
> From: 
> To: 
> Date: Tue, 5 Feb 2008 18:25:08 -0500
> Subject: Test Subject
> Content-Type: text/html; charset="us-ascii"
> Content-Transfer-Encoding: quoted-printable
> Return-Path: DoNotReply@domain.com
> Message-ID: 
> X-OriginalArrivalTime: 05 Feb 2008 23:25:07.0715 (UTC)
> FILETIME=[583C6530:01C8684E]
>
> Any ideas on how to get this working?
>

date: Fri, 8 Feb 2008 10:14:03 -0800   author:   Bharat Suneja [MVP]