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  • Thanks for the information. I have successfully moved/enabled modern authentication (MA) for 3 or the 4 Microsoft 365 tenants I manage. The last has 7 or so users that will not connect with modern authentication. These people are running Outlook 2016, one 2019 on Windows 10 or 11 OS with the latest updates installed.

    Even though these version are said to connect with MA automatically, they are not. I have tried a few different fixes.

    • Deleted any Microsoft credentials
    • added registry keys, even though they are for Outlook 2013
    • Created a new Outlook profile ( Outlook 2019 would not accept the new profile)
    • Uninstalled and reinstall Office 365 the normal way and using the Microsoft support tool

    As a test on one persons Win 10/Outlook 2016 365 I added a new email account to Outlook, which connected with MA, and then exported all from the original to the new. 

    Last day of legacy authentication and not sure how to fix these users issue.

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  • MSouthworth

    Not sure if it is related but a co-worked told me that he had a client that was unable to connect to exchange online via outlook 2016 and he actually had to install a service pack. Might be worth looking into.

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  • kevinweller wrote:

    MSouthworth

    Not sure if it is related but a co-worked told me that he had a client that was unable to connect to exchange online via outlook 2016 and he actually had to install a service pack. Might be worth looking into.

    Thanks, I will see what I can find.

    Pepper graySpice (1) flagReport
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  • Outlook 2016 supports ModernAuth out of the box but Microsoft recommends setting:

    HKEY_CURRENT_USER\Software\Microsoft\Exchange\AlwaysUseMSOAuthForAutoDiscover

    to 1 which will force it to use ModernAuth.

    When I enabled ModernAuth for my tenants years ago there were a few installs (O365 Outlook) that needed their profiles recreated.  Not many but there were a few.

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  • Da_Schmoo​ 

    Thanks for pointing this out I am going to put it in our internal documentation.

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  • Da_Schmoo wrote:

    Outlook 2016 supports ModernAuth out of the box but Microsoft recommends setting:

    HKEY_CURRENT_USER\Software\Microsoft\Exchange\AlwaysUseMSOAuthForAutoDiscover

    to 1 which will force it to use ModernAuth.

    When I enabled ModernAuth for my tenants years ago there were a few installs (O365 Outlook) that needed their profiles recreated.  Not many but there were a few.

    Could swear I added this to the first computer that is having this issue. But have tried so many fixes I can't be sure.. going to check on this. Thanks Da_Schmoo

    Pepper graySpice (1) flagReport
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  • MSouthworth wrote:

    Da_Schmoo wrote:

    Outlook 2016 supports ModernAuth out of the box but Microsoft recommends setting:

    HKEY_CURRENT_USER\Software\Microsoft\Exchange\AlwaysUseMSOAuthForAutoDiscover

    to 1 which will force it to use ModernAuth.

    When I enabled ModernAuth for my tenants years ago there were a few installs (O365 Outlook) that needed their profiles recreated.  Not many but there were a few.

    Could swear I added this to the first computer that is having this issue. But have tried so many fixes I can't be sure.. going to check on this. Thanks Da_Schmoo

    OK, so I took a look at the registry for a couple of users having this issue and there is not a Exchange key in HKEY_CURRENT_USER\Software\Microsoft\. Would I just add that key and then the AlwaysUseMSOAuthForAutoDiscover DWORD? Another thought is to export the Exchange key from a computer that has it, then import it to a computer that does not have it... thoughts?

    Pepper graySpice (1) flagReport
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  • I would assume either way would work.

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