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Outbound mail undeliverable for select domains

Posted on 2009-03-30
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Last Modified: 2013-11-30
We are having problems sending outbound email to select domains.  The emails will sit in Exchange Queue Manager w/ retry until they come back Undeliverable.  We have recently changed our email configuration so that Exchange sends outbound mail instead of a SmartHost.  We prefer using a SmartHost, but we were not able to send any outbound mail after a drive failure.  Please let me know how to troubleshoot this issue.  

I've tried the following already:
1. Enabled Message Tracking and checked history of problem emails.  The following events are repeated every 15 minutes for the domain kalos-inc.com.  "SMTP: Started Outbound Transfer of Message" and "Message transferred to mailserver.kalosinc.local through SMTP".

2. Enabled SMTP logging and compared information in that log to the Message tracking log.

3. Tried SMTPDIAG to test SMTP message flow and no problems during test.

Thanks
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Question by:NKC_USER
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Expert Comment

by:kollenh
ID: 24022252
When you say 'select domains' does that mean that some outbound messages are sent and some are not?  What happens if you try the following on your exchange server:  nslookup -type=mx domain-having-problems.com
You were routing through a Smarthost but changed that; did you create a new outbound connector for your Exchange server to use?  From the message you list, it sounds like it's routing outbound messages back to itself, like it has no outbound path.
HTH
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Author Comment

by:NKC_USER
ID: 24023023
Yes, some outbound messages are sent and some are not.  Between 5 - 10% are not getting delivered.

Nslookup returns
Non-authoritative answer:
kalos-inc.com   MX preference = 10, mail exchanger = mail.kalos-inc.com
mail.kalos-inc.com      internet address = 70.167.62.54

If you're referring to the name mailserver.kalosinc.local that is the recipients server.  I thought it was an odd name for a mailserver ending in .local and somewhat confusing.

Also, I tried connecting to one of the problem mailservers and was able to send an email using telnet.  I received a reply from the user who we are having problems sending to through Exchange.  Not sure why it works thru telnet and not exchange.

Jeff
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Author Comment

by:NKC_USER
ID: 24023097
Forgot to answer question about Smarthost.  We just modified our current connector and removed the Smart host forwarding.
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Expert Comment

by:kollenh
ID: 24023733
That is very strange.  How long has it been since you made the changes?  Have you cycled the Exchange services since then?  I'd look into those domains that aren't going through and see if ".local" are being prepended to all of them.
If you haven't cycled the services since making changes, do so soon as possible.
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Author Comment

by:NKC_USER
ID: 24029932
We made those changes last Monday.  We have rebooted the server several times since then.  

.local is not being appended to any other domains.
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by:Mestha
ID: 24035443
Why did you remove the smart host?
If the message is repeatedly being delivered then that sounds like interference in the SMTP traffic flow. Firewall scanning SMTP traffic can do that.

As for the banner on the remote site, not so unusual. Exchange 2007 requires the use of the local system name on the Receive Connector (inbound email) but uses something else for outbound.

-M
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by:kollenh
ID: 24040532
They removed the smart host because "we were not able to send any outbound mail after a drive failure."  I was assuming Exchange 2003 since that was how it was tagged but probably not a good idea on my part.  For the record, what version of Exchange are you running?
I dont see where anything is mentioned about the message being delivered repeatedly; the problem is that emails to some domains are not being sent with the error message from one example being shown.
Given the message "Message transferred to mailserver.kalosinc.local through SMTP", have you checked other domains to see if the same thing is happening where it's attempting to deliver to a ".local" server name?
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Accepted Solution

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NKC_USER earned 0 total points
ID: 24304923
We did not find a solution to this issue, but assume that the solution using our SmartHost http://www.experts-exchange.com/Software/Server_Software/Email_Servers/Exchange/Q_24278344.html would be the same for this scenario.  Closing question since we found a solution to our original problem.
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