I set up my new email using the TB new email account wizard, which completed successfully. I can receive but not send. I've searched/tried for a while now and no recommendations are working. And I've restarted TB, to no avail. The TB setup wizard came up with these settings: IMAP: Mailserver: outlook.office365.com Port: 993 User Name: mycomplete@email.com (not really) Connection Security: SSL/TLS Auth Method: OAuth2 SMTP: Mailserver: smtp.office365.com Port: 587 Connection Security: STARTTLS Authentication method: OAuth2 User Name: mycomplete@email.com (not really) When I try to send, after a long pause I get "Login to server smtp.office365.com with username X@y.com failed." with the options Retry, Enter New Password and Cancel. When I select 'New Password', I'm never presented with a dialog box for my password. I just get the long pause and "Login to server smtp.office365.com with username X@y.com failed." again.