Creating scheduled messages (alerts) in Learning

Summary

BRAND new user, attempting to mass assign a required course and send scheduled messages (on enrollment, as a reminder X days before its due, etc.)

Content

Greetings. We went live with OC on July 1. We're creating a "course" that everyone with access to the system will have to complete - it's a confidentiality agreement that they need to read / sign / submit. We wanted to use smart language and schedule initial and reminder messages to go out, but are finding it's a much more manual process than that.

Has anyone had success creating and scheduling any messages (alerts) to go out re: assigned learning? What's your secret?