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Delivery has failed to these recipients or groups:

Posted on 2014-03-27
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Last Modified: 2014-06-07
I have a 5 month old sbs 2011 (exchange 2010) machine that has been sending email fine for months. All of a sudden users at work are getting NDR's from exchnage. Nothing has changed. Here is the NDR. Not all emails are rejected.



Delivery has failed to these recipients or groups:

recipient@email.com
The server has tried to deliver this message, without success, and has stopped trying. Please try sending this message again. If the problem continues, contact your helpdesk.








Diagnostic information for administrators:

Generating server: Server.Domain.local

recipient@email.com
#550 4.4.7 QUEUE.Expired; message expired ##

Original message headers:

Received: from Server.Domain.local ([null]) by
 Server.Domain.local (null) with mapi id
 14.03.0174.001; Mon, 24 Mar 2014 08:55:03 -0700
From: user <sender@email.com>
To: "recipient@email.com" <recipient@email.com>
Subject: RE:   Video
Thread-Topic:   Video
Thread-Index: Ac9HeWqGsmfFlGX5T6+vyrgbKrsnYg==
Date: Mon, 24 Mar 2014 15:55:02 +0000
Message-ID: <C937637EEABD7049A9FBE33A292E3F59235E5F0C@ SBS.server.local>
Accept-Language: en-US
Content-Language: en-US
X-MS-Has-Attach:
X-MS-TNEF-Correlator:
x-originating-ip: [192.168.1.114]
Content-Type: multipart/alternative;
      boundary="_000_C937637EEABD7049A9FBE33A292E3F59235E5F0COWLEESBSOWLeelo_"
MIME-Version: 1.0
0
Comment
Question by:Skunny
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14 Comments
 
LVL 9

Expert Comment

by:Mike Roe
ID: 39959232
You need to check and see if you can telnet to port 25 to make sure nothing is blocking the port.
0
 

Author Comment

by:Skunny
ID: 39959260
Telnet failed to connect. I use a barracuda 300 for incoming mail and outgoing goes through exchange 2010.
0
 
LVL 9

Expert Comment

by:Mike Roe
ID: 39959282
Put the IP of the Barracuda in the Default SMTP Connector as a whitelist ip address and see if it changes
0
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LVL 9

Expert Comment

by:Mike Roe
ID: 39959294
Also make sure that the Barracuda trust the IP address of the exchange server.

Other thing to check is AV software.  If it did updates it make be blocking emails.
0
 

Author Comment

by:Skunny
ID: 39960218
I setup a new Send Connector and pointed it to the Cuda. Stopped and restarted the Transport service and everything is now going through the Cuda. But what I do not understand is why I had a ton of emails in the queue with this last error. Of course the queue is empty now.

451.4.4.0 primary target ip address responded with 421.4.4.2

But send just find with the Cuda as the smarthost.
0
 
LVL 9

Expert Comment

by:Mike Roe
ID: 39961481
You may be listed on a blacklist or you have something wrong with your MX records for reverse lookup
0
 

Author Comment

by:Skunny
ID: 39961484
When i run the tools on the MXToolBox everything seems fine.
0
 
LVL 9

Expert Comment

by:Mike Roe
ID: 39961501
can you telnet to port 25 now?
0
 

Author Comment

by:Skunny
ID: 39961506
Cannot telnet into the Barracuda externally but can internally . I can telnet internally to the exchange server.
0
 
LVL 9

Expert Comment

by:Mike Roe
ID: 39961528
Did you have the connector using TLS?  Port 25 blocking and this are usually the reasons for this error
0
 

Author Comment

by:Skunny
ID: 39961698
I have port 25 open to the barracuda for smtp. I do not have TLS on the Exchange connector pointing to the IP of the Barracuda.
0
 
LVL 74

Expert Comment

by:Jeffrey Kane - TechSoEasy
ID: 39971140
First, are the NDR's valid?  Do they actually correspond to an email that was being sent by that user?  If so, you need to start looking for the problem by using the built-in tools in Exchange.

In EMC, open the Toolbox and use the Mailflow Troubleshooter.
0
 

Accepted Solution

by:
Skunny earned 0 total points
ID: 40106432
I fixed this by using the Cuda to send out mail.
0
 

Author Closing Comment

by:Skunny
ID: 40119067
Found answer out myself
0

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