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

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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meinreflection
Asked:
meinreflection
1 Solution
 
IvanSystem EngineerCommented:
Hi,

users are migrated from what/where? Same forest, older exchange?
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noufsCommented:
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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Gareth GudgerCommented:
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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meinreflectionAuthor Commented:
@spriggan13:

Users are moved to Exchange 2010 from non-Exchange system.
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meinreflectionAuthor Commented:
@Gareth Gudger:

Yes
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Gareth GudgerCommented:
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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meinreflectionAuthor Commented:
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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Gareth GudgerCommented:
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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meinreflectionAuthor Commented:
The connection is not very stable and is that normal for unstable connections to experience repeated request for authentication?
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meinreflectionAuthor Commented:
I checked the connection and found it to be unstable.
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