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Coexistence environment - Outlook reconfiguration fail

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We have actually a coexistence environment with ADFS, DirSync and hybrid server. Everything work well excpet the outlook reconfiguration after a migration.

Indeed when we open outlook after the migration to Office 365 the profile is not reconfigured, Outlook stay in disconnected mode without any prompt for credentials.


I can see In outlook logs that the autodiscover is correctly redirect to but the authentification fails with 401 error. Outlook seems to use a login with the format Domain\login and not the UPN


When we manualy do a repair on the profil, outlook prompt for credentials and when we put the login with the format UPN ( the reconfiguration work well.


As our environment is standard, can anyone help us to describe how to re-configure automatically the Outlook client using the Autodiscover as defined in Office 365 Microsoft documents?


Thank you

All Replies
  • Hello,

    The first step, of course, is to make sure that you've run the O365 Desktop Setup on every one of your client computers using O365 and Outlook.  This makes several changes to Outlook (beyond simple Windows Update patches) that might clear this problem up for you.

  • Hello,

    Thank you for your response.

    The problem is still here, even if I install the O365 Desktop Setup before I open outlook.


    Here the log when I open outlook :



    Here the log when I use the repair function on the profile :



    We see that outlook prompt for credentials when we use the repair function.


  • Hello,

    The process for autodiscover should be pointing cloud users to the external autodiscover address using UPN as the credential.  You may want to review and double-check the chapter 'Configure Autodiscover DNS Records' in the Exchange Deployment Assistant for Hybrid configurations:

  • Hello,


    As you can see in the log, Outlook try to connect to office 365 autodiscover. So the configuration of the autodiscover DNS record is ok.

  • Did you ever resolve this issue? I am also seeing this issue. It happens to about 30-40% of the Outlook clients we are flipping at one of our customers.

  • Hello,


    No, the issue is still here. Did you notice a difference between the clients without problems and the ones with ?

  • No, in fact, this issue occurs with WinXP and Win7 machines. It also occurs with Outlook 2007/2010 clients. It would be one thing if it was all or none, but it is not. I'll continue to work on the issue and let you know if I find a solution.

  • We are having the same problem in 4 out of 12 users who we migrated today.  Deleting the profile does not work, as Outlook is unable to recreate it.  The mailbox can not be found via email address, nor even when we put in the O365 server name.  Outlook Anywhere tests successful with REmote Connectivity analyzer

  • Are you still having this issue? We have not seen it lately, but have also not made any changes. When we did have the issue, we were able to recreate the Outlook profile. It almost sounds like you are having an autodiscover issue on those 4 machines. When you do test email auto-config on the machine, does it return autodiscover info for that user?