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Outlook 2010 continually asking for credentials

Posted on 2014-01-15
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Last Modified: 2014-02-01
We have Exchange 2010 in a DAG config.  Users run Outlook 2010 clients.  Over the past few months more and more users complain of being asked for credentials by Outlook continually throughout the day or a few days.  Some people get prompted for the credentials over and over acting like their PW is incorrect.  For these people I add a entry in Windows 7 Credential manager but this is a pain bc when they change PW 90 days later they forget they have this and haven't changed the PW there.  Some people get the pop up prompt then never get it again. It is a random issue, different for everyone considering length and how often and on going issue getting worse for months now.

Any help is appreciated.

Thank you
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Question by:Twhite0909
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by:Simon Butler (Sembee)
ID: 39783676
The entry in credential manager is a kludge and shouldn't really be required if the clients are in the same Forest as the Exchange server.

The primary reason for authentication prompts is issues around SSL certificates or authentication settings on the Autodiscover virtual directory. It can also be caused by DNS issues, where the Autodiscover process looks to the wrong server.

You need to do an Autodiscover test (hold down ctrl while right clicking on the Outlook icon in the system tray) to see what is happening on the client, where it is connecting to.

Simon.
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by:Twhite0909
ID: 39783834
Autodiscover seems to be ok it looks for and finds my cashub server then ow and oof directories successfully.  What am I looking for with my Cert and IIS settings as far as authentication settings on Auto discover Virtual Directory?
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Simon Butler (Sembee) earned 500 total points
ID: 39784699
You are looking for the certificate to be trusted by the client. Do you have a trusted SSL certificate in place?

As it is Exchange 2010, it may well be quicker to reset the Autodiscover virtual directory, as the default settings are usually fine for 99% of implementations.

Simon.
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