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email domain name showing as the wrong address

Hi all,

I have a fairly annoying problem.


Exchange 2003 server - Country A
Domain 1  - example.net
Domain 2 - example.net.au
Domain 3 - different.com

Users - Country A - Domain 1,2   -  No problems
Users - Country B - Domain 3   - Problems

The problem is as follow:

2 of 3 users in Country B, using RPC/HTTP Outlook Anywhere are receiving bounced email from clients / external people. They are sending out as user@different.com but when an external person is sending to them they are getting bounceback email from user@example.net.

Users in Country B are have multiple SMTP address on their AD account, with different.com as the primary. 'Update based on recipient policies' is unticked.

If you need any further information, or this is written so terribly that you can't understand it, please let me know.

I have access to the Exchange server, DNS domain setup etc.

Sample of an error:

-----Original Message-----
From: Mail Delivery System
Sent: 15 February 2011 17:27
To: External User

Subject: Mail delivery failed: returning message to sender

This message was created automatically by mail delivery software.

A message that you sent could not be delivered to one or more of its recipients. This is a permanent error. The following address(es) failed:

    (generated from internal.user@different.com)
    SMTP error from remote mail server after RCPT
    host mx1.xxx.com.au [xxx.xxx.xxx.xx]: 550 #5.1.0 Address rejected.

------ This is a copy of the message, including all the headers. ------

Return-path: <allan.mcewan@spacesolutions.info>
Received: from [] (helo=mail.spacesolutions.info)
      by lon1-post-2.mail.demon.net with esmtp (Exim 4.69)
      id 1PpOgN-00072o-cc; Tue, 15 Feb 2011 17:27:24 +0000
Received: from spacesolutions.info [] by mail.spacesolutions.info - Websense Email Security (7.2.0); Tue, 15 Feb
2011 17:13:01 +0000
Received: from ([]) by chessabz02.chess.group
([]) with Microsoft Exchange Server HTTP-DAV ;  Tue, 15 Feb 2011 17:23:28 +0000
Subject: Proposal
From: "External User" <external.user@spacesolutions.info>
Content-Type: text/plain;
Message-ID: <9560F65B-B183-4CA3-B10B-F93333C6A3A3@spacesolutions.info>
Date: Tue, 15 Feb 2011 17:26:09 +0000
To: <internal.user@www.example.net>,
Thread-Topic: Proposal
Thread-Index: AcvNNQ9zpWKj+sGfQquqQ4oet5/26w==
Content-Transfer-Encoding: quoted-printable
MIME-Version: 1.0 (iPhone Mail 8A293)
X-SEF-7853D99-ADF1-478E-8894-213D316B8FFA: 1
X-SEF-Processed: 7_2_0_00499__2011_02_15_17_13_02
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2 Solutions
your key is here

 host mx1.xxx.com.au [xxx.xxx.xxx.xx]: 550 #5.1.0 Address rejected

my best guess is that mx1.xxx.com.au is some external spam filter and it is not configured correctly for user@different.com, in all cases this is the guy rejecting the messages.

is this mx1.xxx.com.au your exchange server?
samfptAuthor Commented:
the mx.1 address is our Spam/Filtering provider

So you think that is the place where it is being rejected?
I don't think it is written :)

    host mx1.xxx.com.au [xxx.xxx.xxx.xx]: 550 #5.1.0 Address rejected.
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samfptAuthor Commented:
Sorry I don't know what you mean there?
I mean that this line >>  host mx1.xxx.com.au [xxx.xxx.xxx.xx]: 550 #5.1.0 Address rejected. <<<<

means that mx1.xxx.com.au [xxx.xxx.xxx.xx] replied Address Rejected so the problem can only be from the anti spam
samfptAuthor Commented:
Ah ok. Thanks for that, I have previously spoken with them and they seemed to think it was all fine at their end. I will give them another call and get to the bottom of it!

I agree that the junkmail filter is worth checking into.

Also, this may cause you some problems:

Usually, the www prefix is only used for websites. email addresses normally just have example.net (not www.example.net)

I suspect the address is being rejected as it is invalid.
samfptAuthor Commented:

That's what I thought initially, but I've confirmed the user is entering the address correctly and not with a WWW prefix

Should hear back from the Spam provider today and will report back

Thanks all
check the tracking logs in the server. if the user isn't entering the address as www.example.net you need to work out why the www is being added. this is almost certainly the issue.
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