@aparker3
It can be done through the Canvas API (programming type stuff) but not through the web interface and the Assign to box.
I was thinking about that earlier this week when I was splitting students up for small team discussions and wanted to just copy/paste my list of students into the box. I remember last semester when I just typed the first name of a student and hit enter without thinking about it. It turned out that student's first name was completely contained within another student's name and it gave me the wrong student. The one student had no final exam to take while the other had two. This semester, my students have uniquely different (but phonetically similar) first names, but copy/pasting could lead to potential issues if Canvas couldn't resolve the names.
With the Canvas API, you would need the Canvas user IDs, which are guaranteed to be unique, rather than the names. That's not human friendly, but you could get them from a gradebook export. If you have a large class and do this regularly, it may be something to consider. If it's a one-off thing, the development time to write the script may be longer than it takes to add the students manually.
Another option might be to create a script that randomly assigns students across different assignments. I have five small-team discussions and I want each student placed into one of them at random. That has limited use, though. I'm using it for next week's discussion where I don't know anyone and truly want random assignments. For the final, I want to make sure that I control the random nature so that friends don't get the same version.
There's a lot of ways that something like this could be approached, but it definitely is difficult the way it is right now.
