Thanks Patrick and so sorry for the trouble!
I just tried to reproduce the issue on my end, and once I log in, I’m not prompted to log in again unless I’m quitting the Outlook app. Is there any chance you could send a screencast to support team so we can escalate the issue to our development team?
Loom is a great app for video screencasts: https://www.useloom.com/
In your video screencast, we recommend that you use a Chrome Incognito window and have your Javascript console open:
Try to include the entire browser window, including URL bar, in the video screencast.
Thanks you!