Delivery has failed to these recipients or groups:

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
SkunnyAsked:
Who is Participating?
 
SkunnyConnect With a Mentor Author Commented:
I fixed this by using the Cuda to send out mail.
0
 
Mike RoeCommented:
You need to check and see if you can telnet to port 25 to make sure nothing is blocking the port.
0
 
SkunnyAuthor Commented:
Telnet failed to connect. I use a barracuda 300 for incoming mail and outgoing goes through exchange 2010.
0
Free Tool: SSL Checker

Scans your site and returns information about your SSL implementation and certificate. Helpful for debugging and validating your SSL configuration.

One of a set of tools we are providing to everyone as a way of saying thank you for being a part of the community.

 
Mike RoeCommented:
Put the IP of the Barracuda in the Default SMTP Connector as a whitelist ip address and see if it changes
0
 
Mike RoeCommented:
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
 
SkunnyAuthor Commented:
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
 
Mike RoeCommented:
You may be listed on a blacklist or you have something wrong with your MX records for reverse lookup
0
 
SkunnyAuthor Commented:
When i run the tools on the MXToolBox everything seems fine.
0
 
Mike RoeCommented:
can you telnet to port 25 now?
0
 
SkunnyAuthor Commented:
Cannot telnet into the Barracuda externally but can internally . I can telnet internally to the exchange server.
0
 
Mike RoeCommented:
Did you have the connector using TLS?  Port 25 blocking and this are usually the reasons for this error
0
 
SkunnyAuthor Commented:
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
 
Jeffrey Kane - TechSoEasyPrincipal ConsultantCommented:
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
 
SkunnyAuthor Commented:
Found answer out myself
0
Question has a verified solution.

Are you are experiencing a similar issue? Get a personalized answer when you ask a related question.

Have a better answer? Share it in a comment.

All Courses

From novice to tech pro — start learning today.