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Outlook is run by Microsoft, and is obviously suffering from whatever the "update" did to authentication.
Perhaps that wouldn't have happened to Thunderbird. MS supports IMAP, IIRC.
My brother had to reinstall peripheral drivers every month because patches killed them like clockwork. He threw in the towel and ended up with an Ubuntu Linux system sold and supported by Dell, and hasn't called me for help in years. 
He uses outlook.com (MS) as a mail server.
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