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Delivery has failed to these recipients or distribution lists

astrosbs asked

I have a user who keeps on failing to send an email to a particular domain. It's Windows Server 2003 R2 64bit with Exchange 2007. One thing that I notice is that the recipient's domain is blacklisted as spammer. Is there some sort of security policy that blocks him from sending to spammer address? The server has TrendMicro ScanMail software as well. When I use http://zoneedit.com/smtp.html tool to test the SMTP connection it went through. Below is the bounceback message he keeps on getting:


Delivery has failed to these recipients or distribution lists:
Emad Nashed
Microsoft Exchange has been trying to deliver this message without success and has stopped trying. Please try sending this message again, or provide the following diagnostic text to your system administrator.
Sent by Microsoft Exchange Server 2007

Diagnostic information for administrators:
Generating server: parkinson-fs1.parkinson.local
#550 4.4.7 QUEUE.Expired; message expired ##
Original message headers:
Received: from parkinson-fs1.parkinson.local ([]) by
 parkinson-fs1.parkinson.local ([]) with mapi; Fri, 14 May 2010
 11:40:25 +1000
From: Con Sakkas <con@parkinsongroup.com.au>
To: Emad Nashed <Emad.Nashed@kingston.vic.gov.au>
Date: Fri, 14 May 2010 11:36:21 +1000
Subject: FW: Coversheet - Olive Gv,Mentone.pdf - Adobe Acrobat Professional
Thread-Topic: Coversheet - Olive Gv,Mentone.pdf - Adobe Acrobat Professional
Thread-Index: Acry7kzYsWBsez2mS0eOd15/wdI5FAAF2YKA
Message-ID: <26F4338258AB4047AF057C378707D086035357411EBD@parkinson-fs1.parkinson.local>
Accept-Language: en-US, en-AU
Content-Language: en-US
X-MS-Has-Attach: yes
acceptlanguage: en-US, en-AU
x-tm-as-product-ver: SMEX-
x-tm-as-result: No--63.244900-5.000000-31
x-tm-as-user-approved-sender: No
x-tm-as-user-blocked-sender: No
Content-Type: multipart/mixed;
MIME-Version: 1.0
Watch Question

If the recipient is blacklisted, your email system will automatically not speak to that domain.

Notify the domain's IT dept that this is happening and they will have to clean up their spam sources to remove themselves from the blacklists and get email flowing to them again.

If the recipient domain is blacklist, unfortunately its out of your scope.
Only thing you can do is try to contact them and get them to start the process of checking their LAN
Also you can get them to start removing their IP from blacklist as it some times take 24 to 48 hrs to clear


Strange one really. Blacklisting is only usually used when someone sends to you. Very few e-mail systems check if someone is on a blacklist when sending TO them.

I've run a quick test on the details you have supplied and it appears OK at present, but that was from my system so only confirms their system is available.

Do you know how to test the e-mails manually using nslookup & telnet?
if not try this link from your EMAIL SERVER.

This should let you try a test message. This must be done from the server that the emails would be sent from for it to be a proper test.

Open the page, enter the details and click 'begin test'.

from: con@parkinsongroup.com.au
to: Emad.Nashed@kingston.vic.gov.au

after a few moments you will get some text in the bottom half of the window. paste it in here for me.


Yes that is strange indeed. Because from what I know normally email systems only checks incoming emails.

Anyway, as per my original post I have tried using zoneedit.com smtp test tool and here is the result:

SMTP Connection:
OK, connected to
< 220 mail.kingston.vic.gov.au ESMTP MailMarshal (v6.7.2.8378) Ready
> HELO edit.dnsvr.com
< 250 mail.kingston.vic.gov.au Hello edit.dnsvr.com (
> MAIL FROM:<con@parkinsongroup.com.au>
< 250 sender ok <con@parkinsongroup.com.au>
> RCPT TO:<emad.nashed@kingston.vic.gov.au>
< 250 recipient ok <emad.nashed@kingston.vic.gov.au>
< 354 send the mail data, end with .
> From: con@parkinsongroup.com.au
> To: emad.nashed@kingston.vic.gov.au
> Subject: ZoneEdit Automated SMTP Test (

> If you received this, then the mail server ( is probably working.
> Sent at 2010-08-03 08:20:27 by using Mozilla/4.0 (compatible; MSIE 7.0; Windows NT 5.2; WOW64; GTB6.5; .NET CLR 1.1.4322; .NET CLR 2.0.50727; .NET CLR 3.0.4506.2152; .NET CLR 3.5.30729)
> .
< 250 B4c58dcc90000 Message accepted for delivery



Did you run this test from your email server?
This test worked fine and suggests there is no problem which makes it difficult to fix.

The error you mentioned in the question (queue expired etc) means that the server was unable to reach the recipients server.

This could generally be:
*DNS issue, meaning it was unable to lookup the recipients server address
*Connection issue, meaning the connection to the recipients server is not possible
*Junk issue, meaning the recipients server may have a junkmail filter that drops the conneciton from your server without giving a reason (you could be blacklisted, for example)

If you ran the above test on the e-mail server that would be sending the mesage, all three of these came up fine and prove that the server can do a DNS lookup on the address, can connect and can deliver the message!


Yes that is also what confused me. I ran that from the email server and the result of test seemed to tell that there's no problem sending the email. And yet, Outlook ALWAYS gives me that delayed error message. Only to that particular domain though (and not just the one that's sent to Emad Nashed, but all recipients). At the moment I tricked it by creating a POP account in Outlook and everytime they need to send to kingston, they need to choose the POP account instead of through Exchange...
could you set up a send connector specifically for this domain and point it straight to their mail server? it would be interesting to see if this works as this takes a lot of the routing process out of the issue.


Still didn't work. I'll close the question however as the client is not too fuss using the POP account. I'll grant the points to totallytonto. Thanks for your help, mate! Cheers!


Closing the question. Points granted to totallytonto