Managing personal Outlook.com account settings, security, and privacy
Hi,
From what you describe, it almost feels like the sign-in box is losing focus after the first try, which can happen if the browser or app is getting in the way. A couple of things often cause that cached data, extensions like password managers, or even the app itself acting up.
Can I just check a couple of things to narrow it down: are you running into this inside a browser (like Chrome or Edge), or is it happening in the Outlook/Microsoft app on Windows?
Kind regards,