Forum Discussion
Outlook: Permanent prompts to re-enter passwords
Some additional information is needed I'm afraid;
-This profile you're having trouble with, is it correct to say that you have multiple user mailboxes associated with it, including one that's an MFA-enabled administrator?
-Have you tried creating this Outlook profile on a different Windows 10 user profile? With what results?
-Have you tried creating an Outlook profile for a different user (non-Global Admin)? With what results?
Two things occur to me;
1) The same account(s) work on other machines, meaning it's not an issue with the AutoDiscover record. That rules out a lot of transient problems.
2) MFA + Not receiving the MFA prompt on profile creation + Permanent prompts to re-enter passwords = Updates. Ensure that Windows10 and Office365 (I.e. the Office suite installed on the computer) are fully up to date.
It may even be worthwhile trying an app password (instead of the user password) when configuring the Global Admin's Outlook profile. If it works, it's an MFA issue.
The simplest solution, however, is to use Microsoft SARA
https://outlookdiagnostics.azureedge.net/sarasetup/SetupProd.exe
If there are any updates required, it will download them for you. If it fails to create the profile for you, it'll help significantly in narrowing down the issue. Just be sure to select the option for "This is the computer I'm having the issue on". If you don't, SARA will close. Odd design.
Good luck.