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Moving mailboxes stops mail flow - Exchange 2003 to 2010

Posted on 2014-02-15
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Last Modified: 2014-03-28
I have setup an SBS 2011 server with Exchange 2010.  I have in use an Exchange 2003 server that is being decommissioned.

I have transferred the rights and all other settings to the 2010 server and I am now moving the mailboxes.

Unfortunately this is taking a LONG time due to the sizes of the boxes.  While these boxes are moving I was under the impression only the box (or boxes) currently in the process of actually moving would not work while the rest would.

Problems:

1. ALL mail is being held in queue and not being delivered.

2. A box that was already moved continues to ask for a password in Outlook with no result.

3. Using the mail flow troubleshooter provides the following results:

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The 'Remote delivery' queue (LUEMAILSERVER\74) on server LUEMAILSERVER is in retry status. Number of message(s) in the queue: 1. Last error information: 451 4.4.0 Primary target IP address responded with: "421 4.2.1 Unable to connect." Attempted failover to alternate host, but that did not succeed. Either there are no alternate hosts, or delivery failed to all alternate hosts.
==================================
Server mail.guiderail.com is a remote server to which server LUEMAILSERVER is trying to send messages but no 'Host' records of server mail.guiderail.com can be obtained from any DNS servers server LUEMAILSERVER uses. This may be causing message backups in the queue.
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The computer account for Exchange server wfs1.luinc.guiderail.com does not appear to contain the fully-qualified domain name of Exchange SMTP virtual server 'Default SMTP Virtual Server'. This may cause Kerberos authentication to fail when sending messages between servers. The tool expected to find 'SMTPSVC/mail.guiderail.com' in the ServicePrincipalName.
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Remote server mail.guiderail.com failed the mail acceptance test. MAIL FROM command: Respond = 530 5.7.1 Client was not authenticated.
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mail.guiderail.com is the public name and CAN be resolved via pinging/traceroute/etc.

WFS1 is the old server and LUEMAILSERVER is the new server.

Mail CAN be sent out and IS received by outside recipients and mail IS being received just held in queue.

Please advise.  Thanks.
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Question by:adrobnis
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Simon Butler (Sembee) earned 500 total points
ID: 39861607
The key error here is probably the second to last one. On the SMTP virtual server on the old server, ensure the FQDN is the same as the server's REAL FQDN, not the public one. So if the server is called server.example.com, then that is what it needs to be set to.
For inter-server traffic the actual names of the servers are used.

You should have a new Send Connector on the SBS 2011 server if the wizards were used to configure the server.

The password prompt is often due to an issue with Autodiscover. If you have attempted to use an existing host name and that doesn't resolve to the correct server internally, then you will have problems. The prompt doesn't always mean an authentication error, it can often be a sign of other issues, such as SSL trust.

Simon.
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by:adrobnis
ID: 39861630
Thanks Simon.

For Exchange 2003 - where would I find the SMTP Virtual Server on the old server?  I found the "Default SMTP Virtual Server" but no place for an FQDN.

On the Outlook problem if I look at the account settings it is showing the proper server name (new server) and user name and seems to indicate all is well but of course will not let me in.
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by:adrobnis
ID: 39861720
Never mind.  I found the FQDN location for the SMTP Virtual Server and the Outlook problem was due to some Exchange services not running (even though they were set to automatic) on the new server.

All appears well at the moment.  Hopefully when the boxes finish moving the pending email currently pointing at the old server will know to go to the new.

Anything else I need to do to ensure a smooth transition?  Thanks.
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by:Simon Butler (Sembee)
ID: 39861792
Have you replicated the public folders across? A lot of people try to do that after they have moved the mailboxes and wonder why things don't work correctly. Mailbox moves are actually one of the last things that you should do.

Simon.
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by:adrobnis
ID: 39861943
Unfortunately I have not and most of the boxes are already moved,  three left. How can I make sure the public folders work properly. How do I know if we are even using public folders? Besides the OAB I don't think we are...
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by:Simon Butler (Sembee)
ID: 39862883
If you are on Exchange 2003 then you are using public folders. You have to migrate the public folders to the Exchange 2010 server and remove Exchange 2003 before you can even contemplate removing public folders.

If the mailboxes are moved, then use the MoveAllReplicas command in ESM to move the public folders to the Exchange 2010 Public Folder store. If you don't have a public folder store on Exchange 2010, create one, do the move all replicas command, then change the default public folder database on the Exchange 2010 mailboxes to the new server.

http://technet.microsoft.com/en-us/library/gg576862(v=exchg.141).aspx

Simon.
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by:adrobnis
ID: 39863467
Thanks Simon.  I believe I have moved everything except one box.  Unfortunately these are big boxes (15GB) and took 2.5 days to move.  This last box is about the same size.  Would there any problem, mail flow issue, etc.,  if I left this last box on the old server for the week and moved it over this upcoming weekend?

Thanks.
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by:Simon Butler (Sembee)
ID: 39864108
Exchange will co-exist quite happily, so as long as you have mail flow between the servers you should be fine.

Simon.
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by:adrobnis
ID: 39864250
Great! Glad to hear it. :)

I will have to wait for the user of that one box to come into the office this morning to find out if he is having any problems with mail unless there is a way to test it?

I appreciate your help.
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by:adrobnis
ID: 39867232
Very knowledgeable and helpful.
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