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Outlook Pop-Ups (2016) RRS feed

  • Question

  • Recently stood up a couple of 2016 Exchange environments to simulate/test several things including mailbox migrations.  I feel confident that everything is configured correctly, but recently it seems like Outlook pop-ups have started (see details below).  It seems to be random, but can pretty easily be re-created by rebooting a couple of times.

    Environment Details:

    2 Exchange 2016 environments (2 DAGS) single ORG with Outlook 2016 clients (Win10)

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    Things Checked:

    AutoDiscoverServiceInternalUri - https://autodiscover.domain.net/Autodiscover/Autodiscover.xml 

    A record for autodiscover.domain.net

    Exchange Valid SAN certificate that matches the DNS name autodiscover.domain.net

    Exchange certificate associated to the correct Exchange services (IIS & SMTP)

    Remaining Internal/External URLs (like /mapi etc) also match the certificate name mail.domain.com/mapi

    From the client, Outlook Connection status always establishes

    From the client, Outlook Test E-mail AutoConfiguration works as expected

    From the client https://autodiscover.domain.net/Autodiscover/Autodiscover.xml comes up with NO prompt

    From the client no credentials stored in credential manager

    From the client DNS resolution is successful to the Exchange servers (no LB configured DNS RR used)

    From the client OWA & ECP work without issue

    From the client, no always prompt for credentials checked in the Outlook client

    From the client disabled add-ons (does not help)

    From the client launching Outlook in Safe Mode seems to help, but not fix

    Network connection is good (nothing out of the ordinary)

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    Example:

    Logon to a Win10 system.  Not always, but sometimes the pop-up for username/password occurs.  When it does, I can click cancel and Outlook states need password from the bottom right tray.  I can then click on the words "need password" and Outlook connects without me ever supplying credentials.  Once I do that, then I have not seen another pop-up occur UNTIL i reboot.  Once I logon again I may or may not see it.

    Thank you for any guidance or assistance you can provide.  Currently looking into AV possibilities.

    CWT



    • Edited by CrimsonWT Friday, June 19, 2020 7:07 PM
    Friday, June 19, 2020 4:40 PM

All replies

  • Hi CrimsonWT,

    Did this problem occur for specific users, or all users?

    Did you select "Remember my credential"?

    Please follow the steps below and see if the issue is resolved:

    1. Please run the following command line to check the authentication method used by Outlook Anywhere and MAPI over HTTP:

    Get-OutlookAnywhere | FL Identity,*Auth*,*Host*
    Get-MAPIVirtualDirectory | FL Identity,*Auth*,*URL*

    2. Please check if the Autodiscover service is normal, you could hold CTRL and Click the outlook Icon in the system tray and select “Test Email Auto Configuration”, then deselect the “Use Guessmart” and “Secure Guessmart Authentication” and click Test. 

    3. Use ExRCA to check if connectivity is normal, and if there are any errors, it will also display specific error messages.

    About ExRCA: ExRCA.

    4. There may also be an error in the registration list of Autodiscover, please try to changing the registration list.

    About specific steps you could refer to:Unexpected Autodiscover behavior when you have registry settings under the \Autodiscover key.

    5. If none of the above methods succeed, please try to re-create the Outlook profile.

    Regards,

    Lucas Liu


    Please remember to mark the replies as answers if they helped. If you have feedback for TechNet Subscriber Support, contact tnsf@microsoft.com.

    Monday, June 22, 2020 8:02 AM
  • Hi,

    Do suggestions above help? If you have any questions or needed further help on this issue, please feel free to post back. If the issue has been resolved, please mark the helpful replies as answers, this will make answer searching in the forum easier and be beneficial to other community members as well.

    Regards,

    Joy Zhang


    Please remember to mark the replies as answers if they helped. If you have feedback for TechNet Subscriber Support, contact tnsf@microsoft.com.

    Thursday, June 25, 2020 8:09 AM
  • Good morning Lucas,

    After taking everything from the top let me answer your questions and share what I'm seeing.

    Seems to be random on all users (small test environment).  Some users more than others.  The remember password is definitely not set and we also verified that the credential manager had zero credentials.  Below is the output you requested which looks good.

    Identity:                                          SERVER\Rpc (Default Web Site)
    ExternalClientAuthenticationMethod:  Ntlm
    InternalClientAuthenticationMethod:  Ntlm
    IISAuthenticationMethods:                {Basic, Ntlm, Negotiate}
    ExternalHostname:                           mail.domain.com
    InternalHostname:                           mail.domain.com

    Identity:                                           SERVER\mapi (Default Web Site)
    IISAuthenticationMethods:                {Ntlm, OAuth, Negotiate}
    InternalAuthenticationMethods:         {Ntlm, OAuth, Negotiate}
    ExternalAuthenticationMethods:        {Ntlm, OAuth, Negotiate}
    InternalUrl:                                      https://mail.domain.com/mapi
    ExternalUrl:                                     https://mail.domain.com/mapi

    2.  The autodiscover service works on all clients without exception.  We can also browse the autodiscover.xml file without any prompt for credentials.  It all checks out.

    3.  The ExRCA tool is internet based and we do not have internet access in this environment so it cannot be used as far as I'm aware.

    4.  Very interesting as I personally have never browsed these keys.  In the documentation provided in the link, the \Autodiscover subkey it calls out does not exist on any Win10/Outlook2016 clients.  No idea what to think on this as the only thing under the Autodiscover key listed is RedirectServers?

    HKEY_CURRENT_USER\Software\Microsoft\Office\x.0\Outlook\AutoDiscover

    5.  Have recreated the profile a few times now.  Will go back to the registry and delete the user windows profile though to see if a complete wipe helps.

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    Also checked the Service Connection Points in Sites & Service (essentially the Exchange servers) and all of them have the same URI/URL listed for the serviceBindingInformation (https://mail.domain.net/Autodiscover/Autodiscover.xml) which matches the Exchange output from the Get-ClientAccessServer | fl *URI* command.  We are leveraging DNS for the autodiscover lookup instead of an SRV record which I've read is just fine. 

    The only other thing I can think to add is that the autodiscover URL above is different than what we use for /MAPI, /OAB, /ECP, /OWA etc.

    Also, when Outlook is launched and the prompt for User/Password appears, in the background Outlook shows as connected.  When I click cancel and do NOT supply credentials for the user the need password pops in the bottom right corner of Outlook.  When I click on "need password" the status in the Outlook tray updates and says Connected without ever supplying credentials.

    OWA/ECP work great without issue, so the issue appears to be client based.

    Thanks again for the reply and hopefully something that I have stated gives thought to something else to try.

    CWT


    • Edited by CrimsonWT Thursday, June 25, 2020 5:44 PM
    Thursday, June 25, 2020 5:38 PM
  • Hi CrimsonWT,

    1. Please click Remember Password on the interface for entering credentials.

    2. Please try to add your Outlook account in Windows 10.

    Path:Setting->Email&accounts.

    3. Please try to modify the registry.

    Path: [HKEY_CURRENT_USER \ Software \ Microsoft \ Office \ 16.0 \ Common \ Identity]

    “ DisableADALatopWAMOverride” = dword:00000001

    Regards,

    Lucas Liu


    Please remember to mark the replies as answers if they helped. If you have feedback for TechNet Subscriber Support, contact tnsf@microsoft.com.

    Monday, June 29, 2020 11:12 AM
  • Hi CrimsonWT,

    I am writing here to confirm with you how thing going now? If the above suggestion helps, please be free to mark it as an answer for helping more people.

    Thanks for your understanding.

    Regards,

    Lucas Liu


    Please remember to mark the replies as answers if they helped. If you have feedback for TechNet Subscriber Support, contact tnsf@microsoft.com.

    Thursday, July 2, 2020 6:02 AM
  • Heya Lucas,

    Thank you for the suggestions, but I'm not sure they address root cause.  Meaning that for example if we were to select the remember password option, it will save those credentials and technically fix the issue for the time being, but once the user base passwords expire, then it will just break again?

    For #2 I'm not exactly sure what you are wanting me to test and where?  If I copy/paste to run it just references that i need a new app to open this path.

    For #3 modifying the registry seems drastic for a native install of Exchange and Outlook clients.  Would never want to apply this even if it did work since it seems we are addressing the symptom not the root cause?

    I've gonna back through everything again and its all very strange.  Doesn't happen all the time, but enough to be a pain.  If you have any other thoughts please feel free to share as I do appreciate them.  Just didn't want to try non standard configurations for the issue.

    Thanks,

    CWT


    • Edited by CrimsonWT Thursday, July 2, 2020 6:46 PM
    Thursday, July 2, 2020 6:43 PM
  • Hi CrimsonWT,

    1. One possibility that causes Outlook keep prompting for password is no password cached in credential storage. So please try to click Remember Password ,then provide the login credentials to the Windows credential area.

    Path: Open Control Panel->User Accounts->Credential Manager->Windows Credentials.

    2. About add Outlook account in Windows 10, you could set according to the following path:

    Open the Windows settings->Accounts->Email&accounts.

    In addition, I noticed that you have modified the registry before. It should be noted that you need to restart the computer after modifying the registry.


    Regards,

    Lucas Liu


    Please remember to mark the replies as answers if they helped. If you have feedback for TechNet Subscriber Support, contact tnsf@microsoft.com.

    Friday, July 3, 2020 8:40 AM
  • Hi CrimsonWT,

    I am writing here to confirm with you how thing going now? If the above suggestion helps, please be free to mark it as an answer for helping more people.

    Thanks for your understanding.

    Regards,

    Lucas Liu


    Please remember to mark the replies as answers if they helped. If you have feedback for TechNet Subscriber Support, contact tnsf@microsoft.com.

    Wednesday, July 8, 2020 9:21 AM