It used to be that when using mastery paths, if there was only one assignment option as a consequence of a mastery path, that would be assigned to the student automatically. So let's say, if the student fails Assignment 1, Mastery Paths automatically assigns Assignment 1 Retake to that student.
As of today (Aug 30, 2017), when the student fails, the retake isn't assigned until the student goes into Modules and clicks "Choose assignment path" and selects the (one) option available to them.
Is this a bug or a new feature? It actually really messes up the functionality for us. It's a whole lot of needless work for students to "select" the one option available, and now faculty can’t rely on the gradebook to tell us if students need to do the retake or not, because they don’t show up as “needing” the retake until students "opt-in."
Emily Springfield , I didn't have a lot of time to play around with it, but I'm seeing some similar and strange things. I did a little research and the following student guide explains how to pick a path, implying this isn't a bug necessarily - How do I choose an assignment path in a module? Yet, I took a look at the following Instructor guide and it seemed to imply the only time this picking of a path would come up is if you have an OR option - 4152,668299
Yet, this hasn't been my experience and I'm seeing what you are seeing.
If you haven't, turn this in to Canvas Support and then please come back and let me know your ticket number. I'm going to try to get in a ticket today as well and would like to add your ticket number information to my ticket; I'll also share my ticket information!