Using classic Outlook for Windows in business environments
Let me update my strategy: when the bottom right says "Trying to connect...", then I close the pop-up window that I have hidden away, then click on "Needs Password", then enter my password in the pop-up, then it will connect, but then when the pop-up pops up again, I hide it away again. So at least I only have to enter my password once. Not fun, but it's better than not working at all.