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Outlook 2016 (IMAP) not sending email (connected)

My email is hosted with GoDaddy. I have IMAP set up on Outlook 2016. It has worked fine for over a year. All of a sudden, I am getting prompted continuously for a password. Yet I am receiving mail without an issue.

When I do a repair on the account it fails at "searching for settings" the error is;

An encrypted connection to your mail server is not available


Community Team
Community Team

That is actually a pretty common issue with Outlook installations.  Have you tried testing the email from a different computer to see if you're still prompted for a password repeatedly?

You can find a lot of resources on how to deal with this issue on the Microsoft support website: