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Outlook prompting for user name and password

Hey guys

I will try and be as detailed as I can here.  We recently upgraded from Exchange 2007 to Exchange 2013.  Most of the users have Outlook 2010 and 2013 (even mix).

Here is the problem.  People from outside the office can login without being asked for logins and passwords multiple times (twice) every time they open their Outlook.  Phones work perfectly and I can login with Outlook from home to their server without being asked for passwords.  Its the people in the office that keep getting asked for passwords and they are also getting certificate problems in the office.  Its not all users in the office having password prompt errors.  We are in the middle of going to everyone and creating new mail profiles in the hopes that might solve the problem.

If the profiles don't make a difference, do you guys have any suggestions?


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8/22/2022 - Mon
Adam Farage

It is most likely the way you are doing OA authentication (RPC/HTTPS connectivity method, which is the only method to connect into Exchange 2013 since everything is sent over HTTPS protocol, encapsulated).

If a user is using a domain joined computer and logs in, and for some reason they lose connectivity to the Exchange server when the connectivity is reconnected, using the existing Kerberos authentication ticket they can go in without an issue. The catch here is you have to setup the Outlook Anywhere virtual directory to use NTLM, and not Basic: http://technet.microsoft.com/en-us/library/bb123545%28v=exchg.150%29.aspx

If the machine is not part of the domain (the workstation the user is working with) then a re-prompt might still come up. You can save the credentials within the Credential Manager in Windows (on the workstation), but remember to update this when the user changes there password.

Im assuming you are not using a reverse proxy (such as TMG, ISA or UAG) and if you are let me know, since the steps are not as clear cut.

I will check out that link.  Thanks for extremely quick reply :-)

I am not using any reverse proxy btw :-)

Now, I am not certain I am in the right area but here is a command I ran from the Shell.

Get-OutlookAnywhere -Server Ace-Exch-Host1 | fl *internal*

and I got this reply.

InternalHostname                                   :hou-exchange.acontact.com
InternalClientAuthenticationMethod   :NTLM
InternalClientsRequireSSL                      :SSL

Is that the area you are referring to?
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I had to use Microsoft call in support to get this problem fixed.  Unfortunately no one responded to my last post.