Using classic Outlook for Windows in business environments
I suddenly started having the repetitive password prompt problem last week with a brand new computer on which Outlook was working fine. I finally booted up my old computer today, and the same Comcast email account is working with Outlook on that computer, so I knew it had to be a change that was made on the new computer.
I remembered that my anti-virus software recommended turning on their VPN (and I did) around the same time I started having problems.
I turned off the VPN, set up my Comcast email in Outlook again, and viola, I have email again.