troubleshooting Question

After replacing failed Front End Exchange Server, we're experiences several issues sending mail

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plitz1972 asked on
ExchangeEmail ServersEmail Protocols
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We have a single Exchange Organization with a Front End Exchange Server and Back End Exchange Server.  We're using Exchange Server 2003 on Windows Server 2003 Standard Edition for both servers, both have the latest patches and security updates.  The Front End Server also has GFI MailEssentials installed for scanning all incoming email traffic.  

Three weeks ago, the Front End server died and I was unable to recover the server from backups.  I did the research and figured out how to remove the server from AD and Exchange without the server actually being online.  I proceeded to rebuild the server using a different computer name and IP Address to avoid any conflicts if there were any remnants of the old server still lingering in AD.  I made the necessary correction on our Firewall to reflect the name and IP Address changes of the Front End Exchange Server without changing any other settings on said firewall policies.  I spoke with the IT Consultant who originally configured this Exchange Organization to verify how he had it configured, which I have listed below:

1. The Front End received all incoming email for mycompany.com, which scanned the email using GFI MailEssentials and then forwarded the scanned mail to the Back End.

2. The Back End sent all outgoing mail directly without relaying the emails through the Front End.


Prior to the failure of the Front End server, all outgoing email messages received by recipients outside of our organization would have the following info in the email header:

Delivered-To: receiver@gmail.com
Received: by 10.142.102.19 with SMTP id z19cs550179wfb;
        Mon, 14 Apr 2008 06:33:46 -0700 (PDT)
Received: by 10.150.54.6 with SMTP id c6mr6090076yba.112.1208180026053;
        Mon, 14 Apr 2008 06:33:46 -0700 (PDT)
Return-Path: <sender@mycompany.com>
Received: from mail.mycompany.com (mail.mycompany.com [206.178.26.14])
        by mx.google.com with ESMTP id 66si13774207wra.15.2008.04.14.06.33.44;
        Mon, 14 Apr 2008 06:33:46 -0700 (PDT)
Received-SPF: pass (google.com: domain of sender@mycompany.com designates 206.178.26.14 as permitted sender) client-ip=206.178.26.14;
Authentication-Results: mx.google.com; spf=pass (google.com: domain of sender@mycompany.com designates 206.178.26.14 as permitted sender) smtp.mail=sender@mycompany.com
Received: from xbe.mycompany.com ([192.168.128.10]) by mail.mycompany.com with Microsoft SMTPSVC(6.0.3790.3959);
       Mon, 14 Apr 2008 09:33:44 -0400
X-MimeOLE: Produced By Microsoft Exchange V6.5
Content-class: urn:content-classes:message
MIME-Version: 1.0
Content-Type: multipart/alternative;
      boundary="----_=_NextPart_001_01C89E34.2907409C"


Since the replacement of the Front End server, we have been getting several different NDRs on some email addresses:

            "You do not have permission to send to this recipient.  For assistance, contact your system administrator.
            <xbe.mycompany.com #5.7.1 smtp;550 5.7.1 <xbe.mycompany.com>: Helo command rejected: Host not found>"

AND

            You do not have permission to send to this recipient.  For assistance, contact your system administrator.
            <xbe.mycompany.com #5.7.1 smtp;550 5.7.1 <receiver@theircompany.com>... H:DBL [206.178.26.2] Connections originating from dynamically assigned IP addresses are not allowed. Please use your ISP's relay servers.>


After replacing the Front End server, this is the header info in the emails received by outside recipients:

Delivered-To: receiver@gmail.com
Received: by 10.142.71.12 with SMTP id t12cs533610wfa;
        Tue, 12 Aug 2008 05:55:36 -0700 (PDT)
Received: by 10.114.79.18 with SMTP id c18mr4697259wab.86.1218545736132;
        Tue, 12 Aug 2008 05:55:36 -0700 (PDT)
Return-Path: <sender@mycompany.com>
Received: from xbe.mycompany.com (natout.mycompany.com [206.178.26.2])
        by mx.google.com with ESMTP id 9si3195150ywf.2.2008.08.12.05.55.34;
        Tue, 12 Aug 2008 05:55:36 -0700 (PDT)
Received-SPF: fail (google.com: domain of sender@mycompany.com does not designate 206.178.26.2 as permitted sender) client-ip=206.178.26.2;
Authentication-Results: mx.google.com; spf=hardfail (google.com: domain of sender@mycompany.com does not designate 206.178.26.2 as permitted sender) smtp.mail=sender@mycompany.com
Content-class: urn:content-classes:message
Subject: FW: external hard drive question
Date: Tue, 12 Aug 2008 08:55:33 -0400
MIME-Version: 1.0
Content-Type: multipart/alternative;
      boundary="----_=_NextPart_001_01C8FC7A.B547F43C"
Message-ID: <BEB1E4B06AFC8D40B04D7C0534BBBAE71A8B64@xbe.mycompany.com>
X-MS-Has-Attach:
X-MS-TNEF-Correlator:
X-MimeOLE: Produced By Microsoft Exchange V6.5

I have gone through and verified all of the settings that know of to check in Exchange Systems Manager, but I still can not figure out what I'm missing here.  There must be an option to configure on ESM that directs all outgoing mail to mail.mycompany.com at 206.178.26.14, but I don't know where.

Sorry for the long-winded amount of info, but I figured I'd save people the hassle of asking for it later.


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