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Outlook password prompt after upgrade from exchange standard to enterprise

Posted on 2015-02-11
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Last Modified: 2015-02-17
Last night I did an upgraded my Exchange Server 2003 Standard to Exchange Server 2003 Enterprise. Following the upgrade everything appeared fine. But today we noticed that Outlook (2007/2010) is prompting for the password to the Exchange server. The issue does not occur using OWA. I am not using RPC/HTTP. I reinstalled SP2. The really interesting part is that if we cancel the password box and hit send and receive the status changes back to Connected to Microsoft Exchange. All users are local network users and Exchange is not actually sending any mail. It is strictly used for mail/calendar storage and sharing.
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Question by:OTS_Tech
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Expert Comment

by:Information Technology
ID: 40604236
Happens to us all the time when we do something on the exchange server and users are still logged on to their computers. We tell them to log off before we do any updates or maintenance. If somehow any of the exchange services are stopped and restarted then outlook freaks out and ask for the password... No idea if there is a way around this... Rebooting or login off and back on will stop the behavior...
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Author Comment

by:OTS_Tech
ID: 40604278
I have had several people reboot but it is still occurring for them. I will force everyone off tonight and restart at the server and then bring people back online.
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Expert Comment

by:Simon Butler (Sembee)
ID: 40604299
Did you install the post SP2 updates? Microsoft Update should give them to you.

Simon.
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Expert Comment

by:dsnegi_25dec
ID: 40604778
Did you test email configuration.

Can you check event logs if any authentication issue on DC as well on Exchange side.

This behavior occurs if the computer loses network connectivity
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Expert Comment

by:dsnegi_25dec
ID: 40604780
And can try to reset the password for one user ....And check how it works
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Author Comment

by:OTS_Tech
ID: 40605700
I have restarted all machines including the server.
SP2 and all Windows updates are installed.
I am not finding any authentication errors on the server.
I have tried a password reset as well.

The computers do are not losing network connectivity because they are accessing other files without issue and the communication with exchange still functions.

Maybe I need to look into moving to a new clean Exchange 2007 setup. This may help with a future upgrade to Exchange Online.
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Accepted Solution

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OTS_Tech earned 0 total points
ID: 40606525
I found the problem. Over the past several months I have been preparing to move to Exchange Online, and I had set autodiscover on my DNS to point to autodiscover.outlook.com. Following the upgrade to Excahnge 2003 Enterprise, started to look to that domain. I have removed the DNS entry and the problem has been resolved.
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Expert Comment

by:Information Technology
ID: 40607847
Very interesting that this did not happen before the upgrade... Good to know...
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Author Closing Comment

by:OTS_Tech
ID: 40613816
Solved myself.
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