After digging in and trying to find a solution, I think I found one through Powershell: verifying that Modern Authentication is enabled for Exchange Online. Sometimes we take a deep breath, get a cup of coffee, and come back and put in the same app pw we've been using and it works.Īt a company meeting today we were all grumbling this and especially complaining that while Microsoft says that Modern Authentication is enabled in Outlook 2016 and above by default, it doesn't seem to actually work as intended for our Windows users. Sometimes we run the Office Support Assistant tool to get it to work.

Sometimes we need to clear the credential manager. Sometimes it takes 3, 4, or 5 app passwords before Outlook accepts one. They always eventually work, but we run in to various issues during setup. We've used app passwords for our Windows users. Modern authentication seems to work as expected for them - they log in using their regular password, get a code/authenticator prompt, and complete the login. iPhone/Outlook Mobile/Outlook for Mac users have had zero issues. Specifically, we've been struggling with setting up mail profiles for our Windows users who are using Outlook 2016/2019. We've been struggling with rolling out 2FA for our Office 365 clients over the last year or so.

Outlook 2013 2fa