Emails not sending properly: User Inobservatus is experiencing issues with sending emails, receiving an error related to an SSL handshake failure. pfaffman suggests the issue might be due to an invalid SSL certificate for the mail server. After setting up the SSL certificate, Inobservatus still encounters the SSL error, and is unsure about the SMTP username and password configuration. pfaffman notes that the SMTP credentials depend on the mail server configuration, but running discourse-setup should prompt for the sending address.
Maybe it’s a little hard to guess as there are many ways your mail server might be configured. If sounds like it is accessible via many host name but only one has a valid certificate.
If you run discourse-setup it’ll prompt you for the sending address.