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Outlook 2007 keeps asking for username/password

Posted on 2009-12-16
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Last Modified: 2012-05-08
Hi,
After a reboot of the SBS 2008 server, this startet to happen at the clients. They log on to the domain, open Outlook and are asked for credentials. They have to enter this several times before it's accepted.
OWA is working normally with SSL certificate. I also notice that when I set up an email account in Outlook 2007 it's also asking for username/password when it searches for the server. This has been working fine earlier. Is this something to do with the SSL certificate? I see that when I'm asked for credentials, the mail.domain.com is displayed as servername, not the FQDN for the server.
Any suggestions? Thanks a lot!
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Question by:Phoenix76
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by:Glen Knight
ID: 26063376
You need to either ask whoever it is that controls your external DNS to setup an A record for autodiscover.domain.com to point to the external IP address of your router (same as the OWA one)
or setup an internal zone on your DNS for your external domain name and enter an A record for autodiscover into their and point it to the internal IP address of your exchange server.
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Author Comment

by:Phoenix76
ID: 26064069
Hi,
Thanks for reply. I have an internal zone on my DNS for my external domain, domain.com, into this I have a autodiscover.domain.com pointing to the exchange server. Still I get asked for username and password..
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Author Comment

by:Phoenix76
ID: 26064244
Also, if I use the command Get-AutoDiscoverVirtualDirectory, I get the mail.domain.com as the internal URL..Should there be an external URL here as well?
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Expert Comment

by:Glen Knight
ID: 26064317
If you ping mail.domain.com from a client what do you get?
You
may have to clear the DNS resolver by running ipconfig /flushdns

also have a look at: http://forums.msexchange.org/m_1800413213/tm.htm
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Accepted Solution

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Mestha earned 500 total points
ID: 26065091
The autodiscover URL isn't set on get-autodiscovervirtualdirectory - that value should be left alone.
The only autodiscover value that is set is the internal one, which is set as part of the client access server properties. You can see it on get-clientaccessserver |fl
External autodiscover is not under the control of Exchange.

Is the server fully patched? Rollup 9 for Exchange 2007 resolves some prompting issues. It needs to be manually approved in the Updates part of the management console.

Simon.
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Assisted Solution

by:zahroc
zahroc earned 500 total points
ID: 26065299
This was taken from one of the MVP forums. We are trying the solution this evening.

The issue was detected by Microsoft after certain updates had been applied
to SBS2008.
To resolve the issue please install Rollup 9 for Exchange Server 2007
It can be found on the link below:

http://www.microsoft.com/downloads/details.aspx?FamilyID=55320be2-c65c-48bb-bab8-6335aa7d008c&displaylang=en 
Merv Porter [SBS-MVP]
============================
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Expert Comment

by:naughtynat
ID: 26068580
I am having the same issue.

Is there an easy way to see what rollup update has been installed by a version number? or just go into WSUS to see what has been applied? Or into Add/Remove Programs?
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Expert Comment

by:zahroc
ID: 26068727
Check under Windows Update and select "View Update History"
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