Error message:
An encrypted connection to your mail server is not available.
Click Next to attempt using an unencrypted connection.
My workaround for this is to:
1: While Outlook is open, in the Taskbar System Tray there is an Outlook icon (by the clock, possibly hidden where you need to click the arrow to see it). Hold CTRL and right click on it, and pick "Test E-Mail AutoConfiguration...". An example of finding this icon is here: https://repairit.wondershare.com/email-repair/fix-outlook-encrypted-connection-is-not-available.html
2: Put in the email address and password, click the Test button, and finish the authentication so that the test finishes.
3: If successful, close the Add account/profile window you have open and then try again. This has worked for me several times.