https://bugs.winehq.org/show_bug.cgi?id=38568
--- Comment #3 from philrosenberg p.d.rosenberg@gmail.com --- I've attached the console output
The output begins after I hit the "New..." button in the E-mail tab of the Account Settings dialog. The output ends after the Add New E-mail Account dialog indicates (tick) Extablish network connection (cross) Search for myUserName@myHost server settings (info) An encrypted connection to your mail server is not available. Click next to attempt using an unencrypted connection.
There are references in the output to the email account that was created on Outlook's first run when I clicked next and it tried to create an unencrypted connection to the server (which won't sync). I have replaced the email in these references with user@host for privacy's sake.
Phil