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Problem sending email to certain domain : "This message hasn't been delivered yet. Delivery will continue to be attempted"

Posted on 2014-01-16
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Last Modified: 2014-03-12
I have users at my company that have issues sending emails to a certain domain. They get a message back when composing a new message to this domain:


"Delivery is delayed to these recipients or groups:"

and

 "This message hasn't been delivered yet. Delivery will continue to be attempted"

This doesn't happen every time and seems to happen more frequently when composing a new message as opposed to replying to a message from a user at this domain. Does anyone have any ideas on what I can do to troubleshoot this issue?

We are using Exchange 2010 and Outlook 2010
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Question by:Rob Sanders
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Expert Comment

by:Kent Fichtner
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Do you think it could be an issue with their domain not being stable?  You could check with the mx lookup tool.  That can show some issues with domains.

If you have the option you can also try to use a Hotmail or gmail account to email them to test if it is on your end.
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by:dipersp
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Do you send your emails outbound via DNS or do they go through a third-party that handles spam and such?

If sending via DNS, then from your Exchange server, let's do an NSLOOKUP.  Drop to DOS, type NSLOOKUP.  Type set q=mx (This won't give you any response.)

Then type the domain you're sending to, such as domain.com.  The response should be all of the MX records for the domain in question.

Now exit NSLOOKUP and try to ping those MX records and see if they resolve with an IP (I don't care if they actually ping, I just want to make sure we're getting IP resolution.)

Finally, do a telnet to those IPs.  Drop to DOS and type TELNET 1.2.3.4 25 (Or can do a telnet to the MX records, so telnet mail.domain.com 25 if that is one of the mx records.)  If telnet is not a recognized command, you need to add telnet as a Windows feature.  Can do this part from your workstation, don't need to do it from your server.

Finally, when this is happening, have you look at your Exchange queues to see if the message is sitting in there and if it's giving any good info?

Let me know the outcome of these.
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by:dipersp
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Also, using the mx lookup tool is a great idea, but, I ALWAYS like to check what my mail server THINKS the MX records are as well.  So do both just to make sure things match up.
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by:Simon Butler (Sembee)
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First thing I would do is look in the queue viewer and see what the actual error is. The message you have posted doesn't say and is really aimed at the end user.
If you look in the queue viewer, if there is a problem with delivery then it should show.

Simon.
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by:Rob Sanders
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Thank you both for the super fast responses. I did the mxtoolbox and this is what I got back for their domain (i replaced identifying info with x's):

       blacklist       xxxxxxx       Blacklisted by SORBS SPAM        More Info
      https       xxxxxxx       The operation has timed out (https://xxxxxx)        More Info
      dns               xxxxxxx       SOA Expire Value out of recommended range        More Info
      spf               xxxxxxx       A Valid SPF Record was not found        More Info
      smtp       xxxxxxx       Warning - Does not support TLS.        More Info
      smtp       xxxxxxx       5.366 seconds - Warning on Transaction Time        More Info
      smtp       xxxxxxx       Warning - Does not support TLS.        More Info
      smtp       xxxxxxx       5.101 seconds - Warning on Transaction Time        More Info
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by:Rob Sanders
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Also, I don't have all of the administrative access to everything in Exchange unfortunately. I actually have to work with someone else to get them to access the Exchange server and execute some of these troubleshooting steps, so trying some of these solutions may take a little time.

To answer the earlier question, yes, we are using a third party spam filtering solution.
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by:Kent Fichtner
Kent Fichtner earned 166 total points
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I would take that information along with the results from dipersp's tests above and let the company know there might be issues with their domain.
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dipersp earned 334 total points
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Well, the first issue is they are blacklisted by SORBS.  That is their issue and they need to resolve it.  Until that is resolved, you could have problems delivering mail to them.

But yes, you still want to see what's in the Exchange queues.  IF you are using your third party anti-spam product and sending all email out through them, they may also be able to give you more info or they may have a log you can look through for outbound email.
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by:Rob Sanders
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I was able to put a little more effort into troubleshooting this as I was able to get a little more admin access than what I had previously.

I did an nslookup to get the mx record and its IP address. I verified that DNS resolves the mx record to the correct IP address.

Also I was able to telnet successfully to that server on port 25 and receive:

"220 mxrecord ESMTP . . ."

back.

I went into Exchange to look at the Queue Viewer but when I go into it I get this message:

"The term 'Get-Queue' is not recognized as the name of a cmdlet, function, script file, or operable program. Check the spelling of the name, or if a path was included, verify that the path is correct and try again."

Also, it should be noted that this problem doesn't happen every time so its hard to reproduce and troubleshoot.

Any suggestions?
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by:Rob Sanders
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I was able to make some progress with this. It turned out it had something to do with the email filtering service we were using communicating with the recepient's email server.
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