Exchange 2019 and Outlook 2016, 2019 and 2021 Autodiscover

Question

Dear Community,

I have Exchange 2019 CU12 running on Windows Server 2022. All my Outlook 2013 clients are able to autoconfigure their email profile through Autodiscover without any problem, however, my newer clients, Office 2016 and above, are prompted for credentials in order to configure their profile; however, even after providing credentials, I'm prompted again for credentials.

The Autodiscover URI is pointing to the rights URL.

Can anyone advise why my Outlook 2013 works as they should, and new clients don't?

Thank you

b.l

Answer 1

Hi @Bujar Lushta ,

Great to know that the issue has already been resolved and thanks for sharing the solution so that others experiencing the same thing can easily reference this! Since the Microsoft Q&A community has a policy that "The question author cannot accept their own answer. They can only accept answers by others", I'll repost your solution in case you'd like to "Accept" the answer : )     

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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:

**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.

Answer 2

Dear All,

Please note that we finally solved the problem. The problem was with Kerberos authentication and SPN records. Considering that we migrated from Exchange 2013 to Exchange 2019. the legacy Exchange server used Exchange Alternate Service Account and the computer used for ASA was bound with mail.XXX.rks and autodiscover.XXXX.rks.

https://learn.microsoft.com/en-us/answers/questions/75403/exchange-alternate-service-account-(asa)-causing-m

The hit that we received was at the client under event viewer, system log we noticed the following error:

Once we removed the autodiscover.XXXX.net and mail.XXXX.net from ASA computer account, everything went back to normal.

Thank you all for your time and help.

b.l