Hello, I just tested this program's version 4.20 on a Mac running El Capitan and it did send the email having the SSL option selected. I sent the email using the SMTP option and used Gmail as mail server. You may want to check with the email service provider you are using to send the emails and confirm if it supports SSL. Since you are using a Mac you also can use the option "Unix default script" to use the iOS email composer to send the emails.