Problem forwarding mail using a contact in AD

Posted on 2006-05-01
Last Modified: 2008-02-01
We are currently forwarding mail to one of our user's outside mail accounts using an AD Contact.  This works fine until someone sends an e-mail from a yahoo address to this person.  At this point, the outside mail server rejects the message.  I thought for a while that it might be how thier server accepts 8 bit mime messages, but they are able to recieve messages directly from a yahoo sender, so I don't think that is it.
We also have a Barracuda SPAM firewall in place that scans all inbound e-mail.
Destination address:

@@@Here is the bounce back message that a yahoo sender would recieve
From: Add to Address Book Add Mobile Alert
Date: Tue, 14 Mar 2006 14:52:50 -0500
Subject: Delivery Status Notification (Failure)

This is an automatically generated Delivery Status Notification.

Delivery to the following recipients failed.


Reporting-MTA: dns;
Received-From-MTA: dns;
Arrival-Date: Tue, 14 Mar 2006 14:52:47 -0500

Final-Recipient: rfc822;
Action: failed
Status: 5.6.1
Diagnostic-Code: smtp;554 5.6.1 Body type not supported by Remote Host
X-Display-Name: Felsen, Brian

@@@Here is a message that is from a yahoo address that goes through our Forward, to a yahoo address
X-Apparently-To: via; Thu, 20 Apr 2006 10:30:32 -0700
X-Originating-IP: []
Authentication-Results:; domainkeys=pass (ok)
Received: from (EHLO ( by with SMTP; Thu, 20 Apr 2006 10:30:32 -0700
Received: from ([]) by with Microsoft SMTPSVC(5.0.2195.6713); Thu, 20 Apr 2006 13:21:25 -0400
X-ASG-Debug-ID: 1145553675-21656-62-0
Received: from ( []) by (Spam Firewall) with SMTP id E4E45C56DE for ; Thu, 20 Apr 2006 13:21:15 -0400 (EDT)
Received: (qmail 67398 invoked by uid 60001); 20 Apr 2006 17:21:15 -0000
DomainKey-Signature: a=rsa-sha1; q=dns; c=nofws; s=s1024;; h=Message-ID:Received:Date:From:Subject:To:MIME-Version:Content-Type:Content-Transfer-Encoding; b=t6IwRCU2RwUAsRJFNZ+9JRGwbs/VKVR4ShxvbWNJWqYSRICCum3RNDgiv8BWtRIvjVmOmM2NiL8mbBvwpeW52DqkUudnUQHeYQsdjSZwuvCpObubyHMAvQuip635MPQ1C2ST9ZuNPlJN2NCH1znNWtYGfWBru1lGK9xi9LQrgRE= ;
Received: from [] by via HTTP; Thu, 20 Apr 2006 10:21:15 PDT
Date: Thu, 20 Apr 2006 10:21:15 -0700 (PDT)
From: "me me"
X-ASG-Orig-Subj: 1:20 from yahoo via fwd
Subject: 1:20 from yahoo via fwd
MIME-Version: 1.0
Content-Type: multipart/alternative; boundary="0-1001472536-1145553675=:66970"
Content-Transfer-Encoding: 8bit
X-Barracuda-Bayes: INNOCENT GLOBAL 0.0032 1.0000 -1.9998
X-Virus-Scanned: by Barracuda Spam Firewall at
X-Barracuda-Spam-Score: -2.00
X-Barracuda-Spam-Status: No, SCORE=-2.00 using global scores of TAG_LEVEL=1.0 QUARANTINE_LEVEL=1000.0 KILL_LEVEL=3.0 tests=
X-Barracuda-Spam-Report: Code version 3.02, rules version 3.0.11130 Rule breakdown below pts rule name description ---- ---------------------- --------------------------------------------------
X-OriginalArrivalTime: 20 Apr 2006 17:21:25.0794 (UTC) FILETIME=[DA5F8020:01C6649E]
Content-Length: 682

@@@Here is the header from a message that goes directly from a yahoo address to the outside domain's mail server
Delivery-date: Wed, 15 Mar 2006 09:45:53 -0800
Received: from brianf3 by with local-bsmtp (Exim 4.52)
id 1FJa4G-0000T4-56
for; Wed, 15 Mar 2006 09:45:53 -0800
X-Spam-Status: No, score=-2.2 required=5.0 tests=ADDRESS_IN_SUBJECT,AWL,
BAYES_00,HTML_50_60,HTML_MESSAGE autolearn=ham version=3.1.1
X-Spam-Checker-Version: SpamAssassin 3.1.1 (2006-03-10) on
Received: from [] (
by with smtp (Exim 4.52)
id 1FJa4F-0000St-Sg
for; Wed, 15 Mar 2006 09:45:52 -0800
Received: from [] (HELO
by (mxl_mta-1.3.8-10p10) with SMTP id
Wed, 15 Mar 2006 12:45:49 -0500 (EST)
Received: (qmail 87250 invoked by uid 60001); 15 Mar 2006 17:45:48 -0000
DomainKey-Signature: a=rsa-sha1; q=dns; c=nofws;


vPHM2t7tJyQ0+oj9Iobfw= ;
Received: from [] by via HTTP; Wed, 15
Mar 2006 09:45:48 PST
Date: Wed, 15 Mar 2006 09:45:48 -0800 (PST)
From: Elif Savas Felsen
Subject: yahoo to
MIME-Version: 1.0
Content-Type: multipart/alternative;
Content-Transfer-Encoding: 8bit
X-Spam: [F=0.0100000000; heur=0.500(1500); stat=0.010;
Question by:discmakers
    LVL 11

    Expert Comment

    by:NetoMeter Screencasts

    Have you tried to send directly mail from your exchange to ?
    It is possible to have such problems if your firewall is not configured to allow all of the SMTP commands. A typical example is Cisco PIX with the Mailguard feature on.


    Author Comment

    We are able to send directly from our exchange box to  We do not have the Mailguard feature in place.
    LVL 11

    Accepted Solution

    I would suggest as a next step to enable temporary logging on your virtual SMTP server.
    The log will show what you whether there are problems during the communication between the servers. Here is how the log file shows a single incoming SMTP session:
    Of course you can check the SMTP session with a sniffer (ethereal is free) too. Probably following both approaches is the best idea.



    Author Comment

    Thanks, I will try this.

    Featured Post

    Why You Should Analyze Threat Actor TTPs

    After years of analyzing threat actor behavior, it’s become clear that at any given time there are specific tactics, techniques, and procedures (TTPs) that are particularly prevalent. By analyzing and understanding these TTPs, you can dramatically enhance your security program.

    Join & Write a Comment

    Email statistics and Mailbox database quotas You might have an interest in attaining information such as mailbox details, mailbox statistics and mailbox database details from Exchange server. At that point, knowing how to retrieve this information …
    Easy CSR creation in Exchange 2007,2010 and 2013
    To show how to create a transport rule in Exchange 2013. We show this process by using the Exchange Admin Center. Log into Exchange Admin Center.: First we need to log into the Exchange Admin Center. Navigate to the Mail Flow >> Rules tab.:  To cr…
    The video tutorial explains the basics of the Exchange server Database Availability groups. The components of this video include: 1. Automatic Failover 2. Failover Clustering 3. Active Manager

    734 members asked questions and received personalized solutions in the past 7 days.

    Join the community of 500,000 technology professionals and ask your questions.

    Join & Ask a Question

    Need Help in Real-Time?

    Connect with top rated Experts

    23 Experts available now in Live!

    Get 1:1 Help Now