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SMTP Issues with Office 365

I’m having issues setting up SMTP for Office 365 using the Easy WP SMTP plugin. I keep getting the following vague error message.

SMTP connect() failed. https://github.com/PHPMailer/PHPMailer/wiki/Troubleshooting

I’ve looked through most of the Troubleshooting documentation and have had no luck. Please see the image below for the settings I’m using. It seems like other people have experienced the same issue with Office 365. Any ideas?