Absolutely. The legal world even has a term for this already, "Vexatious Litigant" [0]. We need to start applying this to DMCA requests.
I say that as a teacher.
But that's a ton of work, hard to do uniformly, depends a lot on the teacher's training and the number of students, depends a lot on institutional support for teachers....
Only tricky part is that the students themselves shouldn't be able to collaborate since that can lead to one student taking the entire exam and sharing the answers, or many splitting the questions. I guess that could be remedied with question pooling, just requires a bit more effort.
DMCA safe harbor rules are a protection for users/hosts, not content owners. Anyone who gets a takedown notice can ignore it if they think the source is dishonest, and be at no greater risk than they would be without the safe harbor.
The court case is particularly disgusting. He should win and get treble his court fees, though dunno if Canada has that.
But having said that, I feel for schools as they have to do SOMETHING and there is just nothing good. Can’t have just the honor system cuz that’s worked so well. But if these systems are over the top (and they are) what do you do?
I’m glad I’m not having to take tests using this kind of software. I tend to look around at other things when deep thinking. Even if no music on, I use N/C headphones to keep sounds out. Hell, if it’s particular hard problem I might start sub vocalizing as I work it through. All habits that would get me dinged left and right.