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Exchange 2013 password prompt NTLM

Posted on 2014-04-16
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Last Modified: 2014-04-24
I'm implementing a migration of Exchange 2007 to Exchange 2013 , all but a few users are already migrated.

Some users on Exchange 2013 are requested for password on Outlook. Password is accepted after entering , but again prompts after few hours. There is no particular pattern regarding the type of users ,Windows OS,Outlook version.

When I open the 'Connection Status' , it is stuck on 'Referral' connecting at the first password prompt.

IISAuthentication, Internalclientauthentication , Outlook Anywhere are all on NTLM only.

The password prompt was non-existent initially on Exchange 2013 but after we restarted all Exchange servers during maintenance , users were affected with prompts.

Can anyone help me out?
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Question by:jose87
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LVL 63

Expert Comment

by:Simon Butler (Sembee)
ID: 40003693
Password prompt doesn't always mean an issue with authentication.
The most common cause is actually an SSL certificate issue.
Do you have a trusted SSL certificate on the server? If not then you should do. All communication with Exchange 2013 now goes over web services, so an SSL certificate is key.
Outlook cannot always cope with SSL prompts, so will throw the authentication prompt instead.

Simon.
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Author Comment

by:jose87
ID: 40003715
Yes, I have a trusted SSL certifcate on Exchange 2013. Anything else which can be incorrectly configured. It was working all fine untill a week ago when we restarted all servers.
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LVL 63

Expert Comment

by:Simon Butler (Sembee)
ID: 40003777
Restarting the servers shouldn't have caused problems unless you are using something less than Exchange 2013 SP1 on Windows 2012 R2.

Is the server on Exchange 2013 SP1?
Have you configured Exchange to use the host name on the SSL certificate throughout?

Simon.
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Author Comment

by:jose87
ID: 40003807
Yes, the server is on Exchange 2013 SP1.

Exchange 2013 servers use the CAS hostname on the certificate. But , I haven't added Exch 2007 mailbox server on the 'subject alternative names' in the Exchange 2013 certificate?

Can you verify if this is needed?
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LVL 63

Expert Comment

by:Simon Butler (Sembee)
ID: 40003870
You shouldn't need anything from the Exchange 2007 server on the 2013 SSL certificate, as it should proxy through to the other server.
However if you have Outlook Anywhere enabled on the Exchange 2007 server then it needs to either be disabled or using a unique host name.

Simon.
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Author Comment

by:jose87
ID: 40004010
OA is enabled on E2007 server, I'm using legacy hostname for redirections to E2007 as per migration guidelines.
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LVL 11

Expert Comment

by:hecgomrec
ID: 40008119
Your issue is not related to SSL Certificates.

There are well know issues about this, first thing could be the way you rebooted your servers, last one should always be your exchange server.

Also, it could be just your client version.  If you are running office 2007 I will recommend to have all updates done in one of the stations with the problem and use it as your test lab.

I run into this with a customer and find out almost all his stations were not fully updated, once the update was performed outlook will open like is running for the first time, then you will be asked to enter the username and password, select "Remember Password".

This was only needed for users who's mailbox was moved to the Exchange 2013 and office was not fully updated.
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Accepted Solution

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jose87 earned 0 total points
ID: 40011115
The 'Referral' connections were directed at E2007 server, the following link resolved the issue:-http://www.experts-exchange.com/Software/Server_Software/Email_Servers/Exchange/Q_28293986.html

Thank you all for your inputs.
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Author Closing Comment

by:jose87
ID: 40019510
Solution was discovered while browsing experts-exchange site
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