Hi Friends,

I am using two Exchange 2013 Servers with DAG Configuration. From last 2-3 days, some domain users are getting User Name and Password prompt when they open their Outlook, after entering same, Outlook logs in.

But this should not happen? Seems happening with all Databases mounted on both Servers and mixed Outlook versions.

What should i look at?

few of my observations:

I took two Users of same DB. With one user i am able to launch outlook without any issue, it does not ask for user name and password, with other user, Outlook asks for user name and password at every launch.

used same machine for testing.

Hello Ranjit,

Here some ideas:

• check event viewer on the server
• both user are domain joined ?
• same outlook version ?
• version of outlook ?
• what CU of Exchange 2013 ?
• do you use Load Balancer ? or windows network load balancer ?

waiting your update

regards

Hi, 

PFA below update:

• check event viewer on the server. To be checked thoroughly.  It shows some issue with the DB Health
• both user are domain joined ? Yes
• same outlook version ? Yes
• version of outlook ? 2010
• what CU of Exchange 2013 ? Updated till SP1
• do you use Load Balancer ? or windows network load balancer ? No

Hi, 

PFA below update:

• check event viewer on the server. To be checked thoroughly.  It shows some issue with the DB Health
• both user are domain joined ? Yes
• same outlook version ? Yes
• version of outlook ? 2010
• what CU of Exchange 2013 ? Updated till SP1
• do you use Load Balancer ? or windows network load balancer ? No

Hi ,

If it is happening for all the users then we can check the outlook anywhere authentication but in your case it is happening only for some users and and they are splitted across different databases.

1.Please disable internet explorer proxy settings if you have it for the problematic user accounts and restart the outlook to check the results.

2.Then make sure outlook versions is having the up to date service packs which is required to use with exchange 2013.

3.What happens when you try to configure the problematic account on the different machines that is having other mailboxes configured which is working properly?

4.Did you exchange 2013 coexist with exchange 2010 or 2007 ?

5.Have you reconfigured the outlook profile on the same machine on where the issue is occuring ?

6.For checking purpose did you disable and enable the cached mode ?

Hi,

From your description, I recommend you use Outlook safe mode to determine whether the issue is related to add-ins. What's more, I would like to clarify the following things for troubleshooting:

Open Outlook -> File -> Account Settings -> change -> More Settings -> Security -> select the Negotiate Authentication, uncheck the "Always prompt for login credentials" -> connection -> uncheck the "Connect to Microsoft Exchange using HTTP" -> ok

Hope this can be helpful to you.

Best regards,

Hi Friends,

Thank you all for your valuable inputs, i yet to confirm you back the configurations checks you requested me to check. I am working on same and update you shortly...

Just a small Update to share, i have corrected the Internal URLs as webmail.domain.com instead of servernetbiosname.domain.com and also generated Internal CA Certificate and enabled it for IIS on both CAS Servers. Also, we changed Internal Autodiscover URI as webmail.domain.com instead of autodiscover.domain.com. These were the last major changes we did on the Server Side, and after this, few users started reporting Password Prompt issue at first Outlook Launch...Prior to this there was no issue. Can we enable some logging option on Exchange Server Side and test non working user to see what comes under Serve