Canvas has a "Course Pacing" feature that may be helpful to you. Here's a tutorial video: https://community.canvaslms.com/t5/Course-Pacing-Feature-Preview/Feature-Overview-video/ta-p/519335 And an FAQ: https://community.canvaslms.com/t5/Course-Pacing-Feature-Preview/Feature-FAQ/ta-p/519317 But, basically, you don't set specific dates, you set an amount of time from one thing to another, and Canvas will apply the due dates based on the first date that the student enrolls in a course.