Exchange 2019 and Outlook 2016 and above

[blushta]

Dear Community,

I have Exchange 2019 CU 12 running on Windows Server 2022. The problem that we are facing is with Outlook 2016 and above clients that fail when configuring their email profile for the first time. We do not have the problem with Outlook 2013 clients, ware Autodiscover works without problem. The Outlook 2016 and above prompt for username and password, however, no matter how often I provide the right credentials, I'm prompted again and again. Strangely, Outlook 2013 does not have this problem.
When I right click on Outlook with CTRL and run Test Email AutoConfiguration on Outlook 2013 no problem, all URL are correct, when I run against existing Outlook 2016 client I am prompted for credentials.
Can anyone explain why Outlook 2016 and above have Autodiscover issues and Outlook 2013 does not?

Thank you

b.l

[#2]

What is OutlookAnyware's client authentication method set to in Exchange Server 2019?
Try running the following command!
Get-OutlookAnyware

[#3 · Accepted solution]

Dear Tae,
Thank you for jumping in. We finally managed to solve the problem. I post the answer below:

Issue Symptom:

New clients Office 2016 and later are prompted for credentials to configure their profiles. However, even after providing credentials, they are prompted again for credentials.

The client noticed the following error under Event Viewer, System Log:

User's image

**Resolution:**The problem is with Kerberos authentication and SPN records.

Remove the autodiscover.XXXX.net and mail.XXXX.net from ASA computer account, everything will go

back to normal.

[#4]

I am also glad that the problem is solved.
Thanks!