Exchange 2010 delaying/not sending/receiving emails from a single domain

Looking at an SMTP log would help.  If you don't have logging turned on on your server (it's not on by default, IIRC), you can turn it on by editing the properties of your Send and Receive connector(s) and set it to Verbose logging on the General tab.  Then try sending another email to that address. After about 5-10 minutes, look at the SMTP log, searching it for the sending email addresses (i.e., ray@eaglemachines.com and/or rhoy@alleghencydimension.com).  Once you find the appropriate communications for the time frame when you sent the email, you can extract the needed information to a .txt file by finding all of the lines that refer to the same message ID.  Then we can take a look and see if there's any indication as to why the email didn't go through.

The log you would want to look at would be your SMTPSend log, which will be at the following location:

C:\Program Files\Microsoft\Exchange Server\V14\TransportRoles\Logs\ProtocolLog\SmtpSend

The first line of the message communication will look something like this:

2015-03-27T16:03:28.687Z,[Send Connector Name],08D224FB3E3146B8,0,,184.180.46.149:25,*,,attempting to connect

The long number after the connector name is the message ID, 08D224FB3E3146B8 shown above, so you want to find all of the communication with that message ID number.

Thank you for your reply!
I did as you requested, sending a test email to the suspect email address but nothing concerning this send request was written to the SmtpSend log files!  I know this probably makes no sense? I searched by both ray@eaglemachines.com and rhoy@alleghencydimension.com, received nothing for rhoy@alleghencydimension.com (or alleghencydimension). Searching for ray@eaglemachines.com I found some files but nothing associated with hoy@alleghencydimension.com OR EVEN THE TIME THE MESSAGE WAS SENT!

We are now getting 1 immediate "Undeliverable" message shortly after the message is sent and another 1 minute later!  Addresses are correct and nothing was written to either the SmtpSend or Receive logs.
I sent the last test from OWA and got the following information returned:

Undeliverable: TEST EMAIL from Schneider Computer Technologies on behalf of Eagle Machinery and Supply  
Microsoft Outlook  
 
Sent:  Tuesday, March 31, 2015 9:36 AM  
To:  sctuser
Attachments:  
 
 
 
Delivery has failed to these recipients or groups:

rhoy@alleghencydimension.com (rhoy@alleghencydimension.com)
A problem occurred and this message couldn't be delivered. Check to be sure the e-mail address is correct. If the problem continues, please contact your helpdesk.

Diagnostic information for administrators:

Generating server: EAGLESBSSERVER.EagleMachines.local

rhoy@alleghencydimension.com
#554 5.4.4 SMTPSEND.DNS.NonExistentDomain; nonexistent domain ##

Original message headers:

Received: from EAGLESBSSERVER.EagleMachines.local
 ([fe80::417b:7c49:6758:43c4]) by EAGLESBSSERVER.EagleMachines.local
 ([fe80::417b:7c49:6758:43c4%10]) with mapi id 14.01.0438.000; Tue, 31 Mar
 2015 09:36:06 -0400
From: sctuser <sctuser@eaglemachines.com>
To: "rhoy@alleghencydimension.com" <rhoy@alleghencydimension.com>
Subject: TEST EMAIL from Schneider Computer Technologies on behalf of Eagle
 Machinery and Supply
Thread-Topic: TEST EMAIL from Schneider Computer Technologies on behalf of
 Eagle Machinery and Supply
Thread-Index: AdBrt6GV4OrB7zsCQWiomOHnseXoCw==
Date: Tue, 31 Mar 2015 13:36:06 +0000
Message-ID: <C64A1FAF0CDBFD4C84298851BC4986F27CC8A084@EAGLESBSSERVER.EagleMachines.local>
Accept-Language: en-US
Content-Language: en-US
X-MS-Has-Attach:
X-MS-TNEF-Correlator:
x-originating-ip: [70.60.163.90]
Content-Type: text/plain; charset="us-ascii"
Content-Transfer-Encoding: quoted-printable
MIME-Version: 1.0

Actually, it looks like that email address is mistyped.  The domain name is "alleghenydimension.com" - you have an extra letter in there "alleghencydimension.com."

Sorry about that, I will retry!

I resent my test email to: rhoy@alleghenydimension.com and the message was placed in the Messages queue in the Exchange Tools Queue Viewer with following details:


After 20+ minutes, the message was still in the queue and not showing up in the SmtpSend log. I will wait for the message to empty from the Messages Queue and recheck the log at that time and update you with the results.  The message may take several hours or possibly even a day to empty to empty.

If you have anything else you want me to try, please advise.

Look in the message queue viewer, Queues tab, and find the "Last Error" column.  Often this will give you a clue as to why the message delivery has been delayed.

Nothing is listed there, Message Counts are all '0' and no data in the 'Last Error' column. Still have message sent hanging in the Messages queue though.

That sounds kind of weird. Can you take a screen capture of your Queues tab and Messages tab and post it here?

Here you go...
Queues-tab.png
Messages-tab.png

OK - I see the problem.  If you look at the bottom of the Queues tab, you'll see that it says "Items 3 to 4 of 4."  This is a little tricky thing that happens sometimes when you open the Queue viewer.  You have 2 other items in the queues tab that aren't showing.  Click the |< icon at the bottom to make sure you're viewing all of the items and then take another look/screen shot.

Here you go...
Queues-Item-1-to-3-of-3.png
Full-view-of-message.png

WOW! I will look into this, not sure how I missed that? Thank you for your help. I will keep you posted.

Thank you, that fixed it and I learned a few things!

hypercat did a GREAT job helping me resolve this Exchange server issue. He stuck with me all along the way.  He does GREAT work!

Thank you hypercat!

Hey, Gary - thanks for the points and the praise. Glad to be of help.
Cheers!

Deb