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Exchange 2010 vs. Outlook 2007/2010 Check name and Authentication Issues

Posted on 2015-02-12
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Last Modified: 2015-05-15
Hi experts,

Some of my Exchange 2010 users have issues in checking names or constantly needing to re-authenticate as the following scenarios for the following OS + Office (Outlook) configurations:

Can't check name:
1. XP Pro SP3 + Outlook 2010 (Office 2010 Pro Plus)
2. XP Home SP3 + Outlook 2007 (Office 2007 Standard)

Windows authentication dialog box pops up every few minutes:
1. XP Pro SP3 + + Outlook 2007 (Office 2007 Standard)
2.  Win7 Ultimate SP1 + Outlook 2007 SP3 (Office 2007)
3.  Win7 Ultimate SP1 + Outlook 2007 SP3 (Office 2007 Standard)
4.  Win8 Pro + Outlook 2010 Pro Plus
5.  Win7 Ultimate SP1 + Outlook 2007 (Office 2007 Standard)

I don't know why this is happening for half of the migrated users but the rest of them are ok.

Thanks very much

meinreflection
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Question by:meinreflection
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LVL 15

Expert Comment

by:Ivan
Comment Utility
Hi,

users are migrated from what/where? Same forest, older exchange?
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LVL 5

Expert Comment

by:noufs
Comment Utility
Hello,

I see 2 possibilities:
1: Your certificate correpond to the internal and external names ? Same for autodiscover ?
2: When you  hold on "CTRL" and right clik on the Outlook icon close to the date, select : Test autodiscover.
Deselect the 2 guesssmart then enter your credential.
If its not correct, then your autodiscover is misconfigured.

Those 2 points can generate an authentification popup.
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LVL 30

Expert Comment

by:Gareth Gudger
Comment Utility
To clarify, so all your users are on 2010 now. But half of them get logon prompts and half do not?
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Author Comment

by:meinreflection
Comment Utility
@spriggan13:

Users are moved to Exchange 2010 from non-Exchange system.
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Author Comment

by:meinreflection
Comment Utility
@Gareth Gudger:

Yes
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LVL 30

Expert Comment

by:Gareth Gudger
Comment Utility
Are there any differences with the users with problems versus the ones that are fine? Aside from OS and Office combinations?

Are the problem users in one domain and the working users in another domain? Same question for Active Directory sites, are the problem users in one AD site? Same also for DNS. Are the problem users configured for different DNS servers than the working users? Do they connect to different CAS servers in different sites? Are they on different IP subnets? Behind different routers or firewalls?
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Author Comment

by:meinreflection
Comment Utility
the users only use OWA and outlook anywhere to connect.  we performed manual configuration for the outlook clients.
there are outlook 2007 and outlook 2010.  about half works but half keeps getting prompts.  

There are 2 CAS servers with HW load balancers in front at the same site.
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Expert Comment

by:Gareth Gudger
Comment Utility
Can you confirm that your CAS servers are configured identically. Same URLs and same certificates on both. I assume you Exported the certificate from one CAS server and Imported it into the other CAS server?
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Accepted Solution

by:
meinreflection earned 0 total points
Comment Utility
The connection is not very stable and is that normal for unstable connections to experience repeated request for authentication?
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Author Closing Comment

by:meinreflection
Comment Utility
I checked the connection and found it to be unstable.
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