I think password managers matching domains with credentials might help a little here, but it normalizes finding random tabs with "google" asking for creds down below the point of noise. It often happens right as I log in in the morning to go into my first meetings, and I'm rushed.
Somewhere, someone has likely exploited this by now.
We've recently been aquired and the new company uses Outlook. I can't use the desktop app as it constantly asks me to go through the full authentication process. I have to use the web interface which is just fine for me as I mostly use macOS native apps for mail and calendar. I only use outlook to report phishing emails.