Outlook 2016, Windows 10 - no other email accounts (the it guys at work tell me I'm not Old School, I'm Retro) port 995 port 587 - no encryption usually, the password prompt comes up while outlook is opening and continues outlook safe does not work at all - cannot find outlook/saf Outlook 2016 keeps asking for password This is a recent development. Home Outlook 2021 keeps asking for password IMAP account