Exchange server 2016 authenticate with Kerberos require Outlook 2016 input password when connect mailbox

hiennv10 1 Reputation point
2022-02-12T06:56:14.08+00:00

Hello everyone,

Currently, our organization run Exchange Hybrid mode, we deploy Windows Hello for Business, user with on-premise mailbox will connect to Exchange Server using Kerberos. After complete deployment, we encounter issues when user with on-premise mailbox connect to Exchange, Outlook 2016 prompt require input passwords, i cancel prompt and double click to Need Password, Outlook 2016 can connect to Exchange.

Bellow is result my checked:

  1. "Negotiate" configured for both Outlook Anywhere and MAPI virtual directories, I only have 01 server.
  2. Get-MapiVirtualDirectory | Fl authen,InternalUrl,ExternalUrl
    IISAuthenticationMethods : {Ntlm, OAuth, Negotiate}
    InternalAuthenticationMethods : {Ntlm, OAuth, Negotiate}
    ExternalAuthenticationMethods : {Ntlm, OAuth, Negotiate}
    InternalUrl : https://mail.mydomain/mapi
    ExternalUrl : https://mail.mydomain/mapi
  3. Get-OutlookAnywhere| fl InternalClientAuthenticationMethod, authen,InternalUrl,ExternalUrl
    InternalClientAuthenticationMethod : Negotiate
    ExternalClientAuthenticationMethod : Negotiate
    InternalClientAuthenticationMethod : Negotiate
    IISAuthenticationMethods : {Basic, Ntlm, Negotiate}
  4. Get-OrganizationConfig | Fl MapiHttpEnabled
    MapiHttpEnabled : True

Our server run hybrid mode, but OAuth disabled on my server.

I also check configure Kerberos follow link Configure Kerberos authentication for load-balanced Client Access services | Microsoft Learn, i correct configure, Negotiate occur in RpcHttp, HttpProxy, Autodiscover logs. But result of klist only have http/mail.mydomain.com, does not have http/autodiscover.mydomain.com

We only encounter this issues with Outlook 2016, our environment: Exchange Server 2016 CU22, configure Hybrid Wizard Exchange, Outlook 2013 doesn't impact by issues.
Please help me solve this issues.

Exchange Server Management
Exchange Server Management
Exchange Server: A family of Microsoft client/server messaging and collaboration software.Management: The act or process of organizing, handling, directing or controlling something.
7,393 questions
Microsoft Exchange Hybrid Management
Microsoft Exchange Hybrid Management
Microsoft Exchange: Microsoft messaging and collaboration software.Hybrid Management: Organizing, handling, directing or controlling hybrid deployments.
1,918 questions
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2 answers

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  1. Andy David - MVP 142.7K Reputation points MVP
    2022-02-12T17:44:12.3+00:00

  2. hiennv10 1 Reputation point
    2022-03-08T07:17:41.52+00:00

    After I update Outlook 2016 by KB5001998, Outlook 2016 doesn't popup require password for access mailbox.
    Thanks for all support me.

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