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Outlook 2007 keeps asking for credentials for remote connection to server

Posted on 2010-01-12
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Last Modified: 2012-05-08
Having this excact problem (which is solved for SBS2008 SP1):
http://www.experts-exchange.com/OS/Microsoft_Operating_Systems/Server/SBS_Small_Business_Server/Q_24989899.html
and:
http://www.thirdtier.net/2009/12/outlook-repeatedly-prompting-for-authentication/

My customer has the same problem though on a fresh installation of SBS 2008 SP2, so I can't see the cure in this case.

Any help is greatly appreciated.
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Question by:jmateknik
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Glen Knight earned 2000 total points
ID: 26293816
Have you got a UCC/SAN certificate installed? If so does it have the record autodiscover.domainname.com in it?

Also do you have an A recors in your external DNS for autodiscover.domainname.com it should be pointing to the same IP as your Outlook Web Access URL.

For the second prompt you can try the above.
I have had mixed comments some say the first work and some say the second work but the second one seems to be winning at the moment:

http://social.technet.microsoft.com/Forums/en/exchangesvrgeneral/thread/383d130e-869f-4fce-9502-8b340904b0ba


See the section about enabling Kernel Authentication: http://social.technet.microsoft.com/Forums/en-US/exchangesvradmin/thread/0c94187d-bc97-4fa5-9413-e8762a25a360
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Expert Comment

by:Narayan_singh
ID: 26293887
Use Test EmailAutoconfiguration to see if the URLs are set correct , you should be able to open those URLs from IE without any certificate warning.

Set correct URL see the article below :
http://support.microsoft.com/kb/911816

Make sure Autodiscover virtual directory has basic and windows authentication selected.

If you are using self SSL either get a SAN/UCC certificate or install the certificate manually on client machines.



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Author Closing Comment

by:jmateknik
ID: 31676548
This did the job:
http://social.technet.microsoft.com/Forums/en/exchangesvrgeneral/thread/383d130e-869f-4fce-9502-8b340904b0ba

I had an issue similar to this. Win2k3 Ex07. All of my Outlook 2007
users were getting prompted over and over for the username and
password. It wasn't checking the certificate that they had installed
via internet explorer. To fix the problem, I opened IIS on the
Exchange server and checked the following directories under the
default website (the root site(default web site), oab, autodiscover).
Under the directory security tab, click Edit in the Secure
Communications section. I had the require SSL checked and the 128bit
encryption, but under Client Certificates, it was set to ignore. Once
I changed that to Accept for each of the folders, stopped and started
IIS, I stopped being prompted all the time for credentials. Hopefully
this will help someone in the future.

Thanks to you too Narayan for your effort!
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