The title is pretty self explanatory. I know it's possible, because I am enrolled in a class as both Teacher and Student. I am technically a Department Assistant and TA, and the guy who had the job before me must have figured out how to assign me to two roles at once. I am enrolled as a student so I can get graded for the class, and Teacher so I have all the permissions to create assignments and do grading. I need to do the same for the guy replacing me. He's currently enrolled as a Teacher so he can learn the grading system (he's on part time right now), but I need him to be both Teacher and Student so he can also be graded because he's also taking the class. It's just the nature of the job. Canvas is only allowing me to select one role at a time for one person. As I said, I'm currently enrolled as Teacher and Student, so I know it's possible.