Entourage on Exchange 2003: Adds host IPaddress to mail headers causing mail to appear asspam

[dradunsky]

Good day,

I am setting up Entourage 2008 clients to connect to our Exchange server remotely. When the user sends mail the IP of the sending system is added to the header (see "offending entry" below). Since this IP is not the IP address of mail.<company>.com spam filters reject the mail.

How do I keep Entourage from appending this information to the header?

Thank you.

Received: from barracuda.intldata.com (192.168.16.177) by homer.idc.local
 (192.168.16.2) with Microsoft SMTP Server id 8.1.240.5; Mon, 11 Feb 2008
 11:22:03 -0500
X-ASG-Debug-ID: 1202746914-7a0000010000-f6EORo
X-Barracuda-URL: <http://192.168.16.177:8000/cgi-bin/mark.cgi>
Received: from mail.alisongroup.com (localhost [127.0.0.1]) by
 barracuda.intldata.com (Spam Firewall) with ESMTP id DE1BC206A482 for
 <[email protected]>; Mon, 11 Feb 2008 11:21:54 -0500 (EST)
Received: from mail.alisongroup.com (mail.alisongroup.com [72.158.252.66]) by
 barracuda.intldata.com with ESMTP id Sic4Z1JR6eBo5o3f for
 <[email protected]>; Mon, 11 Feb 2008 11:21:54 -0500 (EST)
X-ASG-Whitelist: Sender

offending entry...

Received: from 192.168.1.10 ([192.168.1.10]) by MailTag.alison.local
 ([192.168.1.45]) with Microsoft Exchange Server HTTP-DAV ; Mon, 11 Feb 2008

16:20:29 +0000
User-Agent: Microsoft-Entourage/12.0.0.071130
Date: Mon, 11 Feb 2008 11:20:19 -0500
X-ASG-Orig-Subj: test
Subject: test
From: Administrator <[email protected]>
To: David Radunsky <[email protected]>
Message-ID: <C3D5DFF3.27%[email protected]>
Thread-Topic: test
Thread-Index: Achsyf5BDmtV0c35wEKcXEEp4nqjGQ==
MIME-Version: 1.0
Content-Type: multipart/alternative; boundary="B_3285573619_71388"
X-Barracuda-Connect: mail.alisongroup.com[72.158.252.66]

 

[Adam Bailey]

I am setting up Entourage 2008 clients to connect to our Exchange server
remotely. When the user sends mail the IP of the sending system is added
to the header (see "offending entry" below). Since this IP is not the IP
address of mail.<company>.com spam filters reject the mail.<br>

How do I keep Entourage from appending this information to the header? -snip-
X-Barracuda-URL: <http://192.168.16.177:8000/cgi-bin/mark.cgi>

Entourage isn't appending this, something on your network is. From the name,
I would suspect the Barracuda Spam Firewall. There's a brief mention of it
in the 3.1.08 release notes
(http://update01.barracudanetworks.com/cgi-bin/view_release_notes.cgi?type=firmware&version=3.1.08).

 

[William Smith]

Good day,

I am setting up Entourage 2008 clients to connect to our Exchange server
remotely. When the user sends mail the IP of the sending system is added
to the header (see "offending entry" below). Since this IP is not the IP
address of mail.<company>.com spam filters reject the mail.

How do I keep Entourage from appending this information to the header?

Rather than trying to change the behavior or how Entourage works I
suggest you try to find why your server is rejecting the message.

You've determined that it's rejecting based on an IP address. Your spam
filter may need to be configured differently.

How are your Entourage clients connecting remotely? Via Outlook Web
Access (OWA) or via VPN first? I'm suspecting via VPN. You might
connecting them via OWA using these instructions
<http://entourage.mvps.org/exchange/exchangeathome.html>.

Hope this helps!

--

bill

William M. Smith, Microsoft Interop MVP - Mac/Windows
Entourage Help Page <http://entourage.mvps.org/>
Entourage Help Blog <http://blog.entourage.mvps.org/>

 

[David]

Thanks, Adam,

My problem is that this only happens with Entourage 2008, not 2004. It is
not happening at the server or the Barracuda.

Still looking for a solution since all mail sent to anyone with a spam
filter tags it as spam unless the sender / domian is whitelisted.

Thanks again.

 

[David]

Thank you William,

My problem is that I don't control the spam filters that my users are
sending to.

Entourage is connecting directly to exchange, either from inside the
firewall or outside.
In both cases the additional line is appended to the header.

I need to solve this as the users (those folks that pay the bills) are
chompin' at the bit to move to 08.

Thanks.

 

[dradunsky]

Another modification to the original. This happens whether the client is attached to an Exchange 2003 or 2007 server.

Thanks.