


I haven't gotten this to the point where I can disrupt the least amount of "state" and so perhaps I'm missing something. Seems to be the only workaround is to remove the mail account in Outlook and re-add it. To this, and I don't believe that this is a keychain issue (I've culled any and all related keychain entries) I also at one point went looking for other properties data in the Library directories, removing them, but none of that seemed to work either. It appears to me that while an initial authentication follows the path that includes the MFA process, subsequently Outlook doesn't retain the flag that this is an O365 account and requires this enhanced authentication path. Now, I get a prompt that appears to simply be a password prompt from Outlook - a basic macOS dialog, with my corporate email address pre-filled and password and "save to keychain" checkbox. Everything works fine here.Īt some point, however, apparently I need to reauthenticate. My organization email address and password then prompts me to authorize the login via the Microsoft "Authenticator" app that I'd installed per instructions from the organization on my iOS device.
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Initially, when attempting to "Add" my organization account to Outlook, when entering my organization's email address I see a "personalized" login with the organization logo that appears similar to when activating other Office products and logging in with

I'm having trouble understanding exactly what the path is, so I'll boil it down to what I see: I've been having some issues with login to and use of MS Outlook (it's 16.42 now) since my organization adopted multifactor authentication (MFA) for use outside the corporate network.
