exchange 2016 autodiscover working from workgroup machines not from domain joined machines all on same lan

Maher Ramadan 286 Reputation points
2020-10-26T20:36:31.513+00:00

from a client machine that is on a work group on the LAN i am able to connect to exchange through outlook
this problem is only for outlook so i should be autodiscover, strangely from a domain joined machine it keeps asking for pwd?
any thoughts

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.
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  1. KyleXu-MSFT 26,211 Reputation points
    2020-10-27T06:11:13.957+00:00

    @Maher Ramadan

    Do you try to reconfigure mailbox in Outlook on the domain-joined computer?

    If you cannot reconfigure Outlook profile, could you tell use which step that you get this issue? I also suggest you provide a screenshot about the log of "Test Email Autoconfiguration" to us, it will also help us to narrow down this issue:
    35344-qa-kyle-1027111345.png

    If you could recreate Outlook profile successfully but cannot open Outlook after configuration, or this issue occurs on step three (Log on the mail server) during configure Outlook profile, it means this issue doesn't related autodiscover. It may caused by the Outlook Anywhere/MAPI over HTTP in your organization, I would suggest you provide the result of command below to help us to narrow down the connection issue: 

    Get-OutlookAnywhere -Server exch2016 | fl *Hostname,*Authentication*,*Ssl  
Get-OrganizationConfig | fl MapiHttpEnabled  
Get-MapiVirtualDirectory -Server exch2016 | fl *Authentication*,*url

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  2. Maher Ramadan 286 Reputation points
    2020-10-29T09:56:55.183+00:00

    Hi Kyle and sorry for the delayed response
    not able to create outlook profile keep asking for pwd

    the setup is as follows
    4 exchange severs all 2016 CU18
    2 working fine behind A10 NLB the others are the ones we have issues with and they are out of the NLB - not reachable to users

    i am trying to connect to those by chaining the hosts file to test - example 10.10.10.10 mail.mydomain.com

    so outlook wont go the the VIP DNS record

    during the profile creation outlook asks for pwd and never accepts it
    the moment i will change the hosts file to one of the other servers or remove the config - failing back to VIP - close out look and open it no pwd prompt

    35995-image.png

  3. Maher Ramadan 286 Reputation points
    2020-10-30T15:33:51.443+00:00

    during the profile creation outlook asks for pwd and never accepts it (yes)
    Do you mean that this phenomenon will not occur when bypass you NLB? (no) it will work over the NLB as well as directly, on 2 servers - other 2 are not working!
    Domain joined computer will use DC to DNS resolution, so have a check on DNS manager on your DC server, make sure all needed record could be resolution.(work group PC is having the same DNS server on the NIC)