While this is a nice work around, our environment is rather large. I don't need it often, but it stops that small prompt every time. "AlwaysUseMSOAuthForAutodiscover"=dword:00000001 setting and rebooted, and it only brought up the normal big prompt window once and Outlook logged in just fine. It already had "EnableADAL"=dword:00000001 set in the registry. A couple of days ago, it just decided it was going to start asking repeatedly for the password, and it was the old-style small prompt.
Most recently it was my father-in-law's Win 10 computer that has been running Office 365 for several years without issue. I have had multiple systems need the added "AlwaysUseMSOAuthForAutodiscover"=dword:00000001 setting, even without MFA enabled. If they key does not work you might have to reinstall Office on the offending systems. This key forces outlook to retrieve the modern auth DLLs. If you're getting pop ups when you enable MFA with 365 it's likely more related to this key. I HAVE had to fix broken systems that did not have this registry key for some reason. I've never really had to forcibly enable MA. "AlwaysUseMSOAuthForAutodiscover"=dword:00000001 Use everything between the lines to save as a.
You should then get the big login prompt that asks for email address first, then type of account, then password. Or other Linux mail application that support Modern Authentication.Regarding "We have a few Outlook 2016 users constantly receiving a popup for their password", are they getting the old-style small popup with user name, password, and the checkbox to remember the password? If so, try adding the following settings via a reg file, reboot, then open Outlook. Until this bug is corrected by apple you may need to disable the iCloud Keychain as a workaround. There is a bug in Mac Mail that can cause your Office 365 profile to be deleted if the iCloud Keychain is enabled. Need to upgrade to a new version of macOS or use Outlook Web Access ( ) Mac Mail on OS 10.13 (High Sierra) or earlier Will need to upgrade version or use Outlook Web Access ( ) Will need to upgrade version or use Outlook Web Access ( )
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