I have had this message pop up for one of my old clients I still do support for and I am still the Admin for on their 365 system. Microsoft enforcing MFA in 365 in 12 days message Cloud Computing & SaaS.
The odd thing is, this doesn't happen to everyone, only some people are experiencing this problem. another PC with Outlook 2019 OEM - Try to sign on to Office 365 Outlook 2016 OEM - Try to sign on to Office 365 Outlook 2016 Volume- worked with no issue Outlook 2010 Volume - worked with no issue Office 365 sign on still pop up whenever I try to setup the user's profile. I also changed the host file making sure it's pointing to internal Exchange server. I checked public and internal DNS all point to the internal Exchange server DNS name.
When troubleshooting the problem, I try to create a test email profile and Outlook asked me to sign on to Office 365 page instead of Exchange. it will keep popping up and user eventually just open OWA instead. no email will be download until password is typed in.
The user first reported multiple pop up asking for username and password. We have an internal Exchange 2013 server and have laptops with Outlook 2019 OEM.
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