Now I went to Azure properties ( Azure Properties Opens a new window) and went allll the way to the bottom and clicked on the small " Manage Security Defaults" link. I believe you can click also edit any conditional policy's blocking access directly from here but since mine was a security default, I had to look elsewhere. I clicked on the "Conditional Access" tab and saw the policy name blocking sign in was " Security Defaults". Clicking on the failed sign on displays info on why that login attempt was blocked - In my case, desktop Outlook logins were being blocked by " Conditional Policy Access". I reviewed the sign in logs in Azure ( Azure Sign-In Logs Opens a new window) and saw that the desktop Outlook sign-ins were being recognized as single sign-on instead of multi-factor and that they had a status of failed. Enable modern authentication in O365 admin portal. Clearing credentials/uninstalling/pst fixing did nothing for us. Accessing outlook online still worked fine. After enabled, users were constantly prompted for a password to login to desktop Outlook and it stopped syncing. I recently had this issue after a client enabled MFA for the organization.
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