User gets prompted credentials from HT-CAS server roles

Hi Folks,

Can anyone here please assist me with some explanation as to why after I changed the HT-CAS server role in my DR site, some of my users gets prompted to retype their credentials in their Outlook ?

Here’s the setting as at the moment

Physical SiteA – Domain.com (Main HQ)
HT-CAS1-Prod-VM (AD-Site-A)
HT-CAS2-Prod-VM (AD-Site-A)

CCR-MBX1-Prod-VM (AD-Site-A)

Physical SiteB – Domain.com (DR remote site)
HT-CAS1-DR-VM (AD-Site-A)
CCR-MBX2-DR-VM (AD-Site-A)
Previously the setting is bit different:

Physical SiteB – Domain.com (DR remote site)
HT-CAS1-DR-VM (AD-Site-B)
CCR-MBX2-DR-VM (AD-Site-B)
This was due to the CCR mailbox server needs to be in the same domain for me to be able to upgrade to SP3
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Senior IT System EngineerIT ProfessionalAsked:
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Senior IT System EngineerConnect With a Mentor IT ProfessionalAuthor Commented:
ok, I have fixed the issue by setting the following:

Set-ClientAccessServer -AutoDiscoverSiteScope {AD-Site-A}

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Ram BalachandranCommented:
Have you tried auto discover ?
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Senior IT System EngineerIT ProfessionalAuthor Commented:
Why do I need to so that ?
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Will SzymkowskiSenior Solution ArchitectCommented:
When you added the new CAS/HT server in the DR site do you have the appropriate Certificates present on these servers?

You should have a SAN/UCC cert that has the following entries...
- autodiscover.domain.com
- mail.domain.com

Will.
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Senior IT System EngineerIT ProfessionalAuthor Commented:
Will, what is that certificate for ?

this prompt is from outlook internal user, there is no Outlook Anywhere enabled in all of my CAS server.

Somehow the only server who ask the credential is the DR HT-CAS server, both servers in production are ok.
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Will SzymkowskiConnect With a Mentor Senior Solution ArchitectCommented:
Is this DR site isolated from your production network?

Are the virtual directories on the CAS server set accordingly? Where are they being prompted, from Outlook client?. Have you looked at the connection status on the outlook client to see what servers the client is authenticating to? Also what are your authentication settings set to on your DR servers?

Will.
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Senior IT System EngineerIT ProfessionalAuthor Commented:
Well during the DR test, the core switch link is disconnected so practically there is no connection. That is the reason why we hard coded all of the DR site exchange servers with Site-A to resume the mail flow.

And now the DR test has finished, the link back up and running again, the users across the company is now randomly prompted for pop up to type in their credentials? Not all just random people.
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Senior IT System EngineerIT ProfessionalAuthor Commented:
Yes the users is prompted in Outlook the first time they open the application.

Service Desk team ask those users to close and re open outlook but somehow the issue still remains, more random people is prompted with credentials pop up ?
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Will SzymkowskiSenior Solution ArchitectCommented:
Are the users using Outlook cached mode? Have you treid to re-create the OST file or have your users. Try changing that and seeing if that corrects it.

Will.
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Senior IT System EngineerIT ProfessionalAuthor Commented:
Yes they are all using cached mode Exchange Outlook connection.
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Senior IT System EngineerIT ProfessionalAuthor Commented:
I have found my solution based on the finding that I did myself.
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