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Attachments not arriving in Inbox

Posted on 2009-07-16
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Last Modified: 2012-05-07
Running Exchange 2003 on MS Server 2003, use a Watchguard firewall with SMTP proxy, no other mail checkers.  When a sender at a tech school sends an email to one of my users, the attachments are stripped.  But if he sends it again and cc: me, I get the attachments - but once again, Receiver1 does not.  

I have attached the headers from both of the emails--Receiver1 is the one without attachments, Receiver2 is the one that gets the attachments.  I can't discern from these why it's being stripped - can someone?
Receiver1 Header:
Microsoft Mail Internet Headers Version 2.0
Received: from ExchE1.techschool.edu ([198.150.208.226]) by mail.company.com with Microsoft SMTPSVC(6.0.3790.3959);
	 Tue, 14 Jul 2009 16:58:37 -0500
X-WatchGuard-Mail-Exception: Allow
Received: from ExchH1.TechSchool.Login (10.39.0.221) by
 ExchE1.techschool.edu (10.34.1.226) with Microsoft SMTP Server (TLS) id
 8.1.375.2; Tue, 14 Jul 2009 16:58:31 -0500
Received: from ExchMB.TechSchool.Login ([fe80::31a0:ab58:31c4:fa2e]) by
 ExchH1.TechSchool.Login ([::1]) with mapi; Tue, 14 Jul 2009 16:58:34 -0500
Content-Type: multipart/mixed;
	boundary="_000_F1DF34FBA3020A4389022A1D0794C2F7018231EDA46DEXCHMBMATCM_"
From: Sender Name <sender@techschool.edu>
To: "Receiver1@company.com" <Receiver1@company.com>
CC: "Receiver2@company.com" <Receiver2@company.com>
Date: Tue, 14 Jul 2009 16:58:33 -0500
Subject: RE: Procurement history
Message-ID: <F1DF34FBA3020A4389022A1D0794C2F7018231EDA46D@EXCHMB.TechSchool.Login>
References: <b6e8821f-2637-4b53-a5fe-2b6be1de1ec6@ExchH2.TechSchool.Login>
In-Reply-To: <b6e8821f-2637-4b53-a5fe-2b6be1de1ec6@ExchH2.TechSchool.Login>
Content-Language: en-US
MIME-Version: 1.0
X-WatchGuard-IPS: message checked
Return-Path: sender@techschool.edu
X-OriginalArrivalTime: 14 Jul 2009 21:58:39.0037 (UTC) FILETIME=[3E69B6D0:01CA04CE]
 
--_000_F1DF34FBA3020A4389022A1D0794C2F7018231EDA46DEXCHMBMATCM_
Content-Type: text/plain; charset="Windows-1252"
Content-Transfer-Encoding: quoted-printable
 
--_000_F1DF34FBA3020A4389022A1D0794C2F7018231EDA46DEXCHMBMATCM_
Content-Disposition: attachment; filename="winmail.dat"
Content-Transfer-Encoding: base64
Content-Type: application/ms-tnef; name="winmail.dat"
 
 
--_000_F1DF34FBA3020A4389022A1D0794C2F7018231EDA46DEXCHMBMATCM_--
 
Receiver2 Header:
Microsoft Mail Internet Headers Version 2.0
Received: from ExchE1.techschool.edu ([198.150.208.226]) by mail.company.com with Microsoft SMTPSVC(6.0.3790.3959);
	 Tue, 14 Jul 2009 16:58:59 -0500
X-WatchGuard-Mail-Exception: Allow
Received: from ExchH1.TechSchool.Login (10.39.0.221) by
 ExchE1.techschool.edu (10.34.1.226) with Microsoft SMTP Server (TLS) id
 8.1.375.2; Tue, 14 Jul 2009 16:58:31 -0500
Received: from ExchMB.TechSchool.Login ([fe80::31a0:ab58:31c4:fa2e]) by
 ExchH1.TechSchool.Login ([::1]) with mapi; Tue, 14 Jul 2009 16:58:34 -0500
From: Sender Name <Sender@techschool.edu>
To: "Receiver1@company.com" <Receiver1@company.com>
CC: "Receiver2@company.com" <Receiver2@company.com>
Date: Tue, 14 Jul 2009 16:58:33 -0500
Subject: RE: Procurement history
Message-ID: <F1DF34FBA3020A4389022A1D0794C2F7018231EDA46D@EXCHMB.TechSchool.Login>
References: <b6e8821f-2637-4b53-a5fe-2b6be1de1ec6@ExchH2.TechSchool.Login>
In-Reply-To: <b6e8821f-2637-4b53-a5fe-2b6be1de1ec6@ExchH2.TechSchool.Login>
Content-Language: en-US
Content-Type: multipart/mixed;
	boundary="_006_F1DF34FBA3020A4389022A1D0794C2F7018231EDA46DEXCHMBMATCM_"
MIME-Version: 1.0
X-WatchGuard-IPS: message checked
Return-Path: Sender@techschool.edu
X-OriginalArrivalTime: 14 Jul 2009 21:59:00.0521 (UTC) FILETIME=[4B37E990:01CA04CE]
 
--_006_F1DF34FBA3020A4389022A1D0794C2F7018231EDA46DEXCHMBMATCM_
Content-Type: multipart/related;
	boundary="_005_F1DF34FBA3020A4389022A1D0794C2F7018231EDA46DEXCHMBMATCM_";
	type="multipart/alternative"
 
--_005_F1DF34FBA3020A4389022A1D0794C2F7018231EDA46DEXCHMBMATCM_
Content-Type: multipart/alternative;
	boundary="_000_F1DF34FBA3020A4389022A1D0794C2F7018231EDA46DEXCHMBMATCM_"
 
--_000_F1DF34FBA3020A4389022A1D0794C2F7018231EDA46DEXCHMBMATCM_
Content-Type: text/plain; charset="Windows-1252"
Content-Transfer-Encoding: quoted-printable
 
--_000_F1DF34FBA3020A4389022A1D0794C2F7018231EDA46DEXCHMBMATCM_
Content-Type: text/html; charset="Windows-1252"
Content-Transfer-Encoding: quoted-printable
 
 
--_000_F1DF34FBA3020A4389022A1D0794C2F7018231EDA46DEXCHMBMATCM_--
--_005_F1DF34FBA3020A4389022A1D0794C2F7018231EDA46DEXCHMBMATCM_
Content-Type: image/jpeg; name="image001.jpg"
Content-Description: image001.jpg
Content-Disposition: inline; filename="image001.jpg"; size=4824;
	creation-date="Mon, 06 Jul 2009 16:44:10 GMT";
	modification-date="Tue, 14 Jul 2009 16:58:33 GMT"
Content-ID: <image001.jpg@01C9FE58.F0973BB0>
Content-Transfer-Encoding: base64
 
 
--_005_F1DF34FBA3020A4389022A1D0794C2F7018231EDA46DEXCHMBMATCM_--
--_006_F1DF34FBA3020A4389022A1D0794C2F7018231EDA46DEXCHMBMATCM_
Content-Type: application/pdf;
	name="Proc Hist NSN 1234567890123  7 Jul 09.pdf"
Content-Description: Proc Hist NSN 1234567890123  7 Jul 09.pdf
Content-Disposition: attachment;
	filename="Proc Hist NSN 1234567890123  7 Jul 09.pdf"; size=189354;
	creation-date="Tue, 14 Jul 2009 16:57:54 GMT";
	modification-date="Tue, 14 Jul 2009 16:57:54 GMT"
Content-Transfer-Encoding: base64
 
 
--_006_F1DF34FBA3020A4389022A1D0794C2F7018231EDA46DEXCHMBMATCM_--

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Question by:admineo
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4 Comments
 

Author Comment

by:admineo
ID: 24874092
The attachment was a single .pdf document.
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Accepted Solution

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tallafornia earned 500 total points
ID: 24874775
It looks the attachment for the original user is being converted to a winmail.dat file see link.
http://support.microsoft.com/kb/278061
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LVL 32

Expert Comment

by:dpk_wal
ID: 24875676
Looks like SMTP proxy is the culprit; it would strip anything which is not explicitly allowed; in Policy Manager, under Properties, Incmoing SMTP proxy action; look for headers, content types, based on logs you can know the reason why an email attachment is stripped and can add the same in SMTP policy.

Please let know if you need more details.

Thank you.
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Author Closing Comment

by:admineo
ID: 31604387
This KB article led me to the solution - the format of the email needed to be changed.  Thank you!
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