My last job gave me a windows machine. I tried using Windows Hello for login and... it broke Outlook. Apparently this was a known bug.

My solution? Type my strong password at every reboot and move to using the Yubi key they offered me. Great, I like Yubi keys. Oh, I can't set a security key as my primary means of 2 factor? My options were Hello or using the Microsoft authenticator phone app (couldn't use my other OTP app...). So every single login always started with "Sign in with Hello or use a security key". If using Hello I could just tap my finger and move on (and Outlook might crash silently). If security key I had to go through this dumb process of clicking: "use another device", "security key", "next", "type credentials", "tap security key", "ok". I think that needless "next" button was what really got under my skin. It was already a manufactured problem but an extra dialogue screen that is just doing nothing. Quite Kafkaesque.