First, make sure that you're able to configure your own SMTP server via Raley Configurations → Raley Settings → Outgoing email servers screen. Some servers, like smtp.gmail.com will often require two-factor authentication (https://support.google.com/a/answer/6260879?hl=en) . You will need to disable it.
Once you have you server successfully configured under "Outgoing email servers" you can use it in your Notifications configuration
Make sure that your Jira/SD project workflow transition(s) that you're tracking have a post-function defined which fires a Generic Event.