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Ex2013 messages stuck in drafts

Posted on 2014-11-24
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Last Modified: 2014-11-25
Running EX2013CU6 (new install) in mixed Exchange 2010SP3 environment. Mailboxes have been migrated to 2013 box. Have checked Send and Receive connectors in 2013Box and they appear OK. Can telnet (port 25) into 2013 box from outside but when I use telnet to message a mailbox the message doesn't end up there. All outbound traffic from OWA on the 2013 box ends up in drafts. I have to use OWA as I don't have an Outlook client available to get to the server. Exchange 2013 self-signed cert is deployed to IIS and bound to 443. I can get into mailboxes from internet using OWA just can't send anything. Ex2010 server is still there. Would I be better off uninstalling it? (That is of course if uninstall will run---a miracle)
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LVL 12

Expert Comment

by:benhanson
ID: 40463282
Are you saying you have both ex2010 and ex2013 on the same box?
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Author Comment

by:C. M. "Mickey" Metcalf
ID: 40463330
No. They cohabit the same AD Domain but are on separate physical servers...
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Expert Comment

by:benhanson
ID: 40463335
Have you checked to see if your domain is blacklisted?

http://mxtoolbox.com/blacklists.aspx
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Expert Comment

by:VB ITS
ID: 40463451
May seem like a silly question but have you checked that all the relevant Exchange services are started? What happens when you send an email from a mailbox on the 2010 server to a mailbox on the 2013 server?
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Author Comment

by:C. M. "Mickey" Metcalf
ID: 40463637
None of these comments are applicable; Exchange 2010 is shut down and connectors decommissioned; services are all started. Domain may be blacklisted but checking shows IP addresses that do not belong to this server.
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by:benhanson
ID: 40463666
There is generally no issue having both 2010 and 2013 in the same organization.  Can you still see the messages sitting in the mail queue on the server?  If you are blacklisted, it doesn't matter what the ip address is, mail servers are likely to block attempts to relay/send mail from your domain.  Are you using any kind of external spam filter, either an appliance that you host or a hosted service like Postini/Google Apps?  Did you transition your firewall rules to point smtp to the new box?
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Expert Comment

by:VB ITS
ID: 40463813
Is DNS functioning correctly on the 2013 server? Try using the nslookup tool on the server and see if it resolves external domains properly.
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Author Comment

by:C. M. "Mickey" Metcalf
ID: 40463847
nslookup does resolve external server names to the correct IP address for the external server.
Now MSExecTransportSubm is throwing Event ID: 2017 Outbound authentication failed with error TargetUnknow for Send Connector Mailbox Proxy Send Connector. The authentication mechanism is ExchangeAuth. The target is SMTPSVC/SFDISFS2.local.stokesdalefire.com (which is the FQDN of the Exchange 2013 server) about every 3 seconds. But the only send connector I have is set up simply for Internet for all domains Scoping: *  cost 1 and Source server set to the Exchange 2013 server.
Queue Viewer in Ex2010 servers shows 5 message enqueued. They won't deliver with error 451 4.4.0 Primary target IP address responded with 454 4.7.0 Temporary authentication failure. "attempted failover, etc.
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Accepted Solution

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VB ITS earned 500 total points
ID: 40463921
Is the time (and timezone) correct on the Exchange server? Make sure the time is synchronized within 5 minutes of your DC(s).

Next step to troubleshoot Event ID 2017 issues would be to verify the Service Principal Names (SPNs) on your Exchange server:
Open Command Prompt as an Administrator > type SetSPN -L <Exchange 2013 Server Name> > hit Enter > confirm that the following entries are listed:
- SMTP/<Exchange 2013 Server Name>
- SMTP/<Exchange 2013 Server Name>.company.com
- SmtpSvc/<Exchange 2013 Server Name>
- SmtpSvc/<Exchange 2013 Server Name>.company.com


If you're missing any of the above entries then you'll need to use the SetSPN -A <value> command to register them. May also worth running the SetSPN -X command to remove any duplicate entries.
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Author Closing Comment

by:C. M. "Mickey" Metcalf
ID: 40464903
The solution led me into an investigation that eventually lead me to the answer. In Exchange 2013 there are a number of additional SPNs that need to be registered that weren't on this server and not mentioned in your solution:

SMTP, Smtpsvc, POP, POP3, IMAP, IMAP4, exchange RFR, exchangeAB, and exchangeMDB

Nevertheless you should get the points at the "A" level. Thanks for your help VB ITS and I consider the matter closed. We'll put this one in our Exchange 2013 tips notebook for sure.

As a side note: I am at a loss to explain why MS can't get a product to install cleanly in an AD environment where an Exchange 2010 server is running. This is the fourth Exchange 2013 install we've done and the three that failed and were problems were where Exchange 2010 was running in the domain.
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