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Recurring Outlook to Exchange 2010 Authentications

Posted on 2011-02-21
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Last Modified: 2012-05-11
WInServer2008 R2
Exchange 2010

We went through a reputable consultant lead migration from Exchange 2003 to Exchange 2010 about a month ago.  I will do my best given my skill set to explain what's happening.  All is well with the majority of the 40 or so supported.  However, as far as I know, at least 5 or six people (including myself) are getting repeated authentication dialog boxes from Outlook (a mix of 2007 and 2010 users).  In addition, we have seen some issues when trying to access Out of office alerts from at least one Outlook 2010 user.  It's my understanding that these two issues may be related somehow.

Our consultant came out and re-keyed the certificate - adding all the possible server names - reinstalled the new certificate (two of the three are currently listed as "invalid" amongst the one valid one) and he also configured auto-discovery - thinking that these steps would eradicate most if not all of the problems but they are still present.  For what it's worth, I didn't see a single pop-up dialog box today until I broke connection with the email server over a remote desktop session.  I've received two re-authentication requests from Outlook within the 30 minutes since breaking the connection.

We called in a different consultant to look at the problem with fresh perspective and he seems to feel the issue lies somewhere within the auto-discovery configuration.  

Any all help is appreciated.  Thanks.
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Question by:LTWadmin
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OriNetworks earned 1000 total points
ID: 34947368
Just a long shot, try this tool to determined if there is a problem with autodiscover
https://www.testexchangeconnectivity.com/

I have seen users get authentication dialogs when, 1. I restarted the server or 2. the time on the server is different from the users computer
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by:salaskid
salaskid earned 1000 total points
ID: 34947578
security alert pops up
click view certificate
click install certificate
next
next
finish
ok
ok

that should fix it
if not reset the certificate to the default one given by exchange and repete these steps
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Author Closing Comment

by:LTWadmin
ID: 35083993
This has been a long and ongoing odyssey but at this point and in working with Microsoft, the problem appears to be related to a patch release for Outlook 2007.  Not sure if MS has their arms rapped around this issue yet but here's a reference.  Thanks.

KB2412171 is fixed in - http://support.microsoft.com/kb/2475891 (Description of the Office Outlook 2007 hotfix package (Outlook-x-none.msp): February 22, 2011)
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