Resurrecting this post in 2025! I am using the Apple Mail app on my PowerBook G4 running Leopard. A few years ago I ran it though Leopard Webkit to update the certificates etc and it works fine on Gmail if I use an app password. Recently, I tried to add my Hotmail back on and I can't get it to work at all, even with app passwords. I use this Hotmail address with Thunderbird etc without problems. Has anyone managed to get Outlook emails to work with this recently and if so, what settings did you use?