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Constant Username and Password Pop up in Exchange 2007

Posted on 2009-12-18
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Arround three weeks ago I installed a new SBS 2008 Server running Exchange 2007.  All worked 100% flawless for the first few weeks and all of a sudden these past few days I get a constant pop up when opening any of the Outlook 2007 clients asking for a username and password.  I had set up the A record for the Remote web workplace as remote.domain.com.  The username and password prompt that is coming up shows this remote.domain.com at the top.  I have tried disabling Outlook Anywhere at the client machines but it still does it.  All machines also fail the autoconfiguration in Outlook as well as using the Outlook Out of Office Assistant .  The simple work arround is to press cancel to the username and password prompt, then it shows "Need Password" at the bottom right hand side and then hitting Send/Receive connects to Exchange with the message "Online with Microsoft Exchange".  The pop ups are poping up regularyl again though a few minutes later.  Nothing new has been installed except for some security patches from Microsoft.  The remote web workplace is working when typing in https:\\remote.domain.com.  I cant find anyhting in the Event viewer and the entire system runs 100% flawless otherwise.  Any ideas ?  I am at a loss.
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Question by:Lounger-Master
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Expert Comment

by:MCSA2003
ID: 26085793
Not for sure if you have tried this yet but it may be worth a shot. I had the exact same issue just a couple days ago and I searched high and low and followed several articles in which none worked. I rebooted the server and the problem went away.
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Author Comment

by:Lounger-Master
ID: 26085921
I have tried that already.  Rebooted several times actually.  Also power cycled the router.  No luck : (
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Expert Comment

by:Raghuv
ID: 26086070
What happens when you enter the Username and password on the prompt? Does it accept it and asks for authentication again after few minutes ? If yes, then you need to check the authentication on IIS Manager for OAB (Only Integrated Auth), EWS (Only Integrated Auth) & Autodiscover (Basic + Integrated Auth).

In case it does not accept the authentication the first time itself, then try to follow the below KB articles,

Outlook 2007 prompts you repeatedly for a password under certain network conditions
http://support.microsoft.com/kb/956531

You are repeatedly prompted to enter your credentials when you try to connect to an Exchange mailbox by using Outlook 2007
http://support.microsoft.com/kb/927612

Also what's the issued to URL on the certificate installed on the Default Web site? if its "remote.domain.com", then Outlook will prompt for the same.
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eddie_86 earned 2000 total points
ID: 26086117
Make sure you update the Exchange server 2007 with update rollup 9.

You can do it from SBS management console and update it and reboot the machine. That should fix the issue.
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Expert Comment

by:Alan Hardisty
ID: 26086655
What authentication methods have you got setup in your EWS virtual directory in IIS?
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by:Rob Williams
ID: 26087438
There have been many recent reports of Outlook 2007, with SBS 2008, continuously requesting the user re-enter their credentials. In many cases this can be resolved by installing or re-installing Exchange 2007 update rollup 9. It can be found in the following link.
http://www.microsoft.com/downloads/details.aspx?FamilyID=55320be2-c65c-48bb-bab8-6335aa7d008c&displaylang=en
If tempted to install Exchange 2007 SP2, there are several problems with doing so. Best to wait for Microsoft to release an SBS installation wrapper, but if you wish to do review the following first.
http://blogs.technet.com/sbs/archive/2009/08/25/how-to-install-exchange-2007-service-pack-2-on-windows-small-business-server-2008.aspx
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Expert Comment

by:Mestha
ID: 26088436
Don't install Rollup 9 from the manual download as that can cause problems with an SBS Server.
SBS 2008 is designed to be updated with its own updating tool. Go in to Updates in the management console and approve rollup 9 for installation.

You shouldn't mix manual download installations and Windows Update installations. One or the other should be used for patching Exchange.

Simon.
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by:Rob Williams
ID: 26088538
>>"Don't install Rollup 9 from the manual download as that can cause problems with an SBS Server."
Is that true? Not disagreeing but very good information to know.
On a couple of occasions this update has already been applied. Rnd re-applying has been necessary, and resolved the issue. You may not have a choice but to apply manually if the update has already been approved and installed. A few others have reported it didn't show up in WSUS, though I am not sure why that would be the case.
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Author Comment

by:Lounger-Master
ID: 26088703
Thank You everyone for oyur suggestions and comments.  Eddie86 you were the first one to respond with the proper solution.  Sadly I accidentally awareded the points to alanhardisty.  I'll contact Exprest Exchange to get this fixed.  Thank You again everyone.  Fortunately a simpler fix than anticipated !!!!

Thank You all again !
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LVL 76

Expert Comment

by:Alan Hardisty
ID: 26088764
I have requested attention and asked for the question to be re-opened.
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Author Closing Comment

by:Lounger-Master
ID: 31668021
Thnaks so much, this did the trick !
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Expert Comment

by:cstechnet
ID: 26312716
http://support.microsoft.com/kb/956531 Sorted the issue for us.
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