Hi @Francesco Russo ,
Welcome to our forum!
I have some users who on Outlook Desktop occasionally and randomly get the login screen popping up and it goes into a loop for a few minutes.
According to your description, i understand that you encounter the issue where passwords keep popping up, right? If so, please first check if the users have updated their passwords recently. If they didn't, please refer to this official article to troubleshooting: Why does Outlook keep prompting for password.
If not, would you please provide a screenshot of it for our better research? (In order to avoid privacy leakage, please remember to hide your personal information.)
I have already run the troubleshooting tools from the Microsoft website and it seems that the problem is with the client.
Which tool did you run? And are there any analysis results that can give you tips on how to troubleshoot?
It's suggested that you could try to use the Microsoft Support and Recovery Assistant, which works by running tests to figure out what's wrong and offers the best solution for the identified problem.
Hope the above help!
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