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Exchange 2007 to 2013 Co-Existence Issues

Posted on 2014-11-24
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Last Modified: 2014-11-26
I am in the middle of migrating from 2007 to 2013.  Both servers are up and running.  I have mail flowing between them successfully, as well as out to the internet.  I have moved a few users from 2007 to 2013.  My question is once I moved the user mailbox the server name in Outlook changes to a weird name (not the new server name as I would expect).  It prompts for Outlook to close and then re-open.... and then asks for credentials..... and then connects.  When I go to the server settings I see the server name changed, but it looks like a crazy Hex thing....

What is that?  and will it change again once I remove the old exchange server from the Org?  Why prompting for credentials?
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Question by:BSModlin
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by:BSModlin
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Here is a screenshot... The new exchange server name is exchange.abc.comOutlook
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by:it_saige
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Outlook clients no longer connect to a server FQDN as they have done in all previous versions of Exchange. Outlook uses Autodiscover to create a new connection point comprised of mailbox GUID, @ symbol, and the domain portion of the user’s primary SMTP address. This simple change results in a near elimination of the unwelcome message of “Your administrator has made a change to your mailbox. Please restart.” Only Outlook 2007 and higher versions are supported with Exchange 2013.
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This will not change when the Exchange 2007 server is taken offline.  As for prompting for credentials, this is most likely happening because of a discrepancy with the authentication methods.

-saige-
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by:BSModlin
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Ok, so how will my SSL certificate successfully authenticate the internal Outlook users if Outlook is configured to this "connection point" rather than the name?
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by:it_saige
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SSL is not responsible for client authentication.
The Client Access server in Exchange 2013 functions much like a front door, admitting all client requests and routing them to the correct active Mailbox database. The Client Access server provides network security functionality such as Secure Sockets Layer (SSL) and client authentication, and manages client connections through redirection and proxy functionality. The Client Access server authenticates client connections and, in most cases, will proxy a request to the Mailbox server that houses the currently active copy of the database that contains the user's mailbox. In some cases, the Client Access server might redirect the request to a more suitable Client Access server, either in a different location or running a more recent version of Exchange Server.
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With regards to Exchange 2013 and prompting for credentials.  You might check here for helpful tips.

http://ilantz.com/2013/06/29/exchange-2013-outlook-anywhere-considerations/

-saige-
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by:it_saige
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Secure Sockets Layer (SSL) is a method for securing communications between a client and a server. For Exchange Server 2013, SSL is used to help secure communications between the server and clients. Clients include mobile phones, computers inside an organization's network, and computers outside an organization's network.
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-saige-
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by:BSModlin
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I'm sorry for asking, but with the above copy/paste... what does that mean for me... I am still kinda confused....
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by:it_saige
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Not a problem.  What are you confused about?

-saige-
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by:BSModlin
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I have a valid GoDaddy cert installed and changed all of the virtual directories to match the external URLs... I am also using split brain DNS and have the external name of the server and the autodiscover A records pointing to the exchange server.  OWA is configured and accepts the SSL certificate as expected.... Currently when I launch Outlook on a mailbox that has been migrated it is prompting to authenticate with the 2007 server SSL.... then it asks for credentials... and then it connects..... why is that?
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by:it_saige
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Ok, so my first inclination is to believe that the client believes that Autodiscover is still pointing at the Exchange 2007 server and not the Exchange 2013 server.  As for prompting for user credentials, it is because there is either:
A.  A discrepancy with the authentication methods on the client vs the Exchange 2013 server.
B.  The client cannot connect to the public folders (I'm assuming) on the Exchange 2007 server.

What is the client outlook version and client os version?

-saige-
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by:BSModlin
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Windows 7 Pro 64 bit and Outlook 2013
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by:it_saige
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Also, on the client run outlook /rpcdiag.  When it prompts for the username and password see if the mail has an established connection but the Public Folders types has a disconnected status.

Example RPCDIAG output:Capture.JPG
-saige-
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Gareth Gudger earned 250 total points
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Hey BSModlin,

That screenshot is completely normal. That is what the server field looks like in Exchange 2013 on Outlook clients.

This forum thread might help explain.
https://social.technet.microsoft.com/Forums/exchange/en-US/9c77d52a-e717-4423-bed5-fade33e96676/exchange-2013-outlook-2007-server-name-guid?forum=exchangesvrgeneral
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by:BSModlin
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One more question.... Can I migrate mailboxes during production..... While users are using their Outlook? What will happen during, and after the mailbox moves?
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by:Gareth Gudger
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That's a good question. I think it was only Exchange 2010 and newer that allowed you to do live migrations. I think if the source is 2007 it will take the mailbox offline during the move. Could be wrong. Memory is failing me. Let's see what other experts say.
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by:it_saige
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Your memory serves you well Gareth.  ;)

http://blogs.technet.com/b/exchange/archive/2010/07/19/3410438.aspx

http://blogs.technet.com/b/schadinio/archive/2010/07/20/exchange-moving-mailboxes-exchange-2007-vs-exchange-2010.aspx

Online Mailbox Moves were possible starting with Exchange 2010.  This is when the Mailbox Replication Service was introduced.

-saige-
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