Domain users cannot get email to another domain user

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]
zuberlawAsked:
Who is Participating?

[Product update] Infrastructure Analysis Tool is now available with Business Accounts.Learn More

x
I wear a lot of hats...

"The solutions and answers provided on Experts Exchange have been extremely helpful to me over the last few years. I wear a lot of hats - Developer, Database Administrator, Help Desk, etc., so I know a lot of things but not a lot about one thing. Experts Exchange gives me answers from people who do know a lot about one thing, in a easy to use platform." -Todd S.

Jason WatkinsIT Project LeaderCommented:
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.
0
zuberlawAuthor Commented:
Thanks.  I will look into this further, and report back.
0
IT Pros Agree: AI and Machine Learning Key

We’d all like to think our company’s data is well protected, but when you ask IT professionals they admit the data probably is not as safe as it could be.

apache09Commented:
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
0
zuberlawAuthor Commented:
I did try that earlier, Apache09.  It didn't work, but thanks for the suggestion.
0
apache09Commented:
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
0
zuberlawAuthor Commented:
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.
0
apache09Commented:
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
0
zuberlawAuthor Commented:
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.
0
apache09Commented:
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
0

Experts Exchange Solution brought to you by

Your issues matter to us.

Facing a tech roadblock? Get the help and guidance you need from experienced professionals who care. Ask your question anytime, anywhere, with no hassle.

Start your 7-day free trial
zuberlawAuthor Commented:
Thanks for all the help.  The answer is likely DNS related.  You all got me 70% home.
0
It's more than this solution.Get answers and train to solve all your tech problems - anytime, anywhere.Try it for free Edge Out The Competitionfor your dream job with proven skills and certifications.Get started today Stand Outas the employee with proven skills.Start learning today for free Move Your Career Forwardwith certification training in the latest technologies.Start your trial today
Exchange

From novice to tech pro — start learning today.