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Outlook 2013 -Exchange 2013 NTLM Stuck on NTLM Auth method

Posted on 2014-02-06
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Last Modified: 2014-03-03
I keep getting prompted for my user ID and password because proxy auth method is set to NTLM.  We are trying to move over to Exchange 2013 and I'm one of the betas.  With our old Exch 2007 server and older outlook I could just set this to basic auth and the setting would stick.  Does anyone know why I can't get this setting to be persistent?  Thank you.
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Question by:amigan_99
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Will Szymkowski earned 500 total points
ID: 39839537
Do you have your Exchange 2013 CAS server setup with the proper certs? When you introduce any new Exchange server version into your environment configuring the CAS is the first step you need to do.

Authentication issues happen due to a few things
- Virtual Directories set with the proper authentication
- Certificates are correct for Exchange

If you have Exchange 2013 and 2007 in the same environment I would assume that you have setup your certs in the following way...
- autodiscover.domain.com
- mail.domain.com
- legacy.domain.com

Your CSR should be created from the new Exchange server (SAN Cert) and then imported to the 2013 CAS server (or load balancer if used) and also on your Exchange 2007 CAS server/s.

You will then need to change the virtual directories on Exchange 2013 to match what you had on Exchange 2007 (ews, owa, powershell, eas etc).

Then on your Exchange 2007 server you will then modify your Virtual Directories to point to legacy.domain.com/ews, legacy.domain.com/eas etc.

When users connect they will contact Exchange 2013 first and get re-directed if they have a mailbox on Exchange 2007.


Also when you are opening your Outlook and getting prompted hold ctrl+right click the outlook icon in the system tray and select "connection status" This will show you what servers your Outlook client is authenticating to.

If you use Basic Authentication on Exchange 2007 for RPC over HTTP (outlook anywhere) you will need to change this to NTLM.

Will.
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by:amigan_99
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Thank you.
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