Mail is connecting to your email service provider, but it can’t connect your email account because your email provider isn’t accepting your email password. If Mail on your Mac keeps asking for your password Mail may say that it can’t connect to your email account, and repeatedly ask you to enter the password for it. So, I was having this BRUTALLY annoying issue on my macs (when I work from home, I work on my mac) where, every time I launched Outlook 2016, I would be prompted to login with my credentials… Just super annoying and unnecessary.
