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Domain users cannot get email to another domain user

Posted on 2012-04-02
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Last Modified: 2012-08-13
Hello, all.

I have an odd issue where Exchange 2010 users are unable to email just 1 user on the same domain and server.  Here is the email message we all get when we try to send to USER1.

NOTE that they also get these same message if they email the user in question at his other business email address that we do not host or support.

Any ideas?

Thanks!

M.J.
================================================
Delivery has failed to these recipients or groups:

USER 1
A communication failure occurred during the delivery of this message. Please try resending the message later. If the problem continues, contact your helpdesk.

Diagnostic information for administrators:

Generating server: server.DOMAIN.com

USER1@domain.com
#< #5.5.0 smtp;550 Unrouteable address> #SMTP#

Original message headers:

Received: from server.mail.DOMAIN.com ([192.168.2.5]) by server.DOMAIN.com
 with Microsoft SMTPSVC(6.0.3790.4675);       Mon, 2 Apr 2012 12:03:20 -0700
Received: from server.mail.DOMAIN.com ([fe80::60e9:8fe2:1056:30aa]) by
 server.mail.DOMAIN.com ([fe80::60e9:8fe2:1056:30aa%10]) with mapi id
 14.01.0289.001; Mon, 2 Apr 2012 12:03:19 -0700
From: "USER 2" <USER2@domain.com>
To: "USER 1" <USER1@domain.com>
Subject: Test
Thread-Topic: Test
Thread-Index: Ac0RA0OO+3paZN4pRe+q0bK25R1LTw==
Date: Mon, 2 Apr 2012 19:03:18 +0000
Message-ID: <7FB6585B68A2CD4FB55D9DD19BBA3446A3926147@server.mail.DOMAIN.com>
Accept-Language: en-US
Content-Language: en-US
X-MS-Has-Attach:
X-MS-TNEF-Correlator:
x-originating-ip: [192.168.2.76]
Content-Type: multipart/alternative;
      boundary="_000_7FB6585B68A2CD4FB55D9DD19BBA3446A3926147ZTSVR05domainz_"
MIME-Version: 1.0
Return-Path: USER2@domain.com
X-OriginalArrivalTime: 02 Apr 2012 19:03:20.0125 (UTC) FILETIME=[44D8DED0:01CD1103]
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Question by:zuberlaw
11 Comments
 
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Assisted Solution

by:Red_Tech
Red_Tech earned 40 total points
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LVL 27

Assisted Solution

by:Jason Watkins
Jason Watkins earned 60 total points
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I would make sure your e-mail servers and the DNS servers they use can resolve the domains of the target organization. Once you know the IP address of the DNS servers for the target domain, you can create a conditional forwarder to that zone.
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Author Comment

by:zuberlaw
Comment Utility
Thanks.  I will look into this further, and report back.
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LVL 47

Expert Comment

by:apache09
Comment Utility
User on the same domain and Server....

Im thinking it could be an email cache issue

Have one of the senders open an email
Start Typeing the email address
When it comes up
highlight and delete the autocomplete email address that appears

Now click on To:
Go to the Global Address List
Find the recipient here

Then select the recipient and add them to the To Field

Now send the email
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Author Comment

by:zuberlaw
Comment Utility
I did try that earlier, Apache09.  It didn't work, but thanks for the suggestion.
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LVL 47

Expert Comment

by:apache09
Comment Utility
In that case, might pay to check the users AD Account
Make sure the mailbox is not hidden, or deactivated.

Alternatively, I would also try creating a New SMTP Email Address in their Account
Call it USER.1@domain.com

Set it as the default

Now try this SMTP Address
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Author Comment

by:zuberlaw
Comment Utility
When I turn off the forwarding setup on his domain email account, the email goes through properly to his domain email box.  The forwarding to the exterior email account (SMTP) fails, if I have forwarding on to the Mail Contact.
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Expert Comment

by:apache09
Comment Utility
Is the forwarding account a different address?

If this user is on the same domain, any reason forwarding is on?

If the User address, and the forwarding address is the same shouldnt need to be on.

If the forwarding address is an externl address, you may need to check that Exchange has been setup to allow forwarding to external addresses
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Author Comment

by:zuberlaw
Comment Utility
Sorry, to be more clear, there are two email addresses in play.

On the 2010 Exchange Server there is User1@domain.com and a Mail Contact that goes offsite to another domain, say User1b@otherdomain.com.

The forwarding is on, because the user is more an associate of our company than he is an in office staffer.
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Accepted Solution

by:
apache09 earned 400 total points
Comment Utility
Right then

So the email is being forwarded from your domain to an external domain.

User get the error when autoforwarding is on

and users get the error when they email the user directly using 1 of 2 email addresses they have for this user

If this is the case its likely not an Permission Restricting AutoForwarding to external domains  (would pay to check anyhow)

The issue would tend to tell me its directly related to the external partys exchange server and or even ISP.

You can try to determine (for Them) if its specific to this user or their entire domain

You can do this may finding or locating several other contacts of the external domain and send test messages to these email addresses
If you receiv ethe same response back, the issue is likely with their enitre exchange server and or ISP

If you can sucesfully send to other users of their domain, you will need to get them to check their users setup in the AD or Their Exchange server.

I would also try, logging into an Free ONline POP account (hotmail-Gmail-Yahoo) and send the user an email
If you get the same response the issue is deffinatley on their end.

Unfortunaltey, in such cases these issues become really difficult for one to troubleshoot offsite.

I would simply advise them of your findings, and get them to sort it
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Author Closing Comment

by:zuberlaw
Comment Utility
Thanks for all the help.  The answer is likely DNS related.  You all got me 70% home.
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