I can't remember the name of the web app for my calculus homework, but this was the only one I kind of liked, and ironically it was free. I think it might have been webwork. And in a CS class we used Perusal, which I liked as well, but the grading was an awful black box.

The others cost several hundred dollars, sometimes per semester. I remember the immense frustration of my Spanish professor, who sent an email to their support at least once a week. Their answer was always "We only support Firefox"

That did not stop dozens of students from using Chrome and Safari, myself included. I remember once getting frustrated with the homework, so I wrote a little JavaScript to brute force a question. The security was generally awful.

My fondest memory was using Github to submit assignments, and later as a TA to grade these assignments. Much less friction.

Obviously, I think college professors are looking for a way to reduce their burden of creating assignments and grading, but these education giants put out poor quality apps, knowing they'll generate revenue regardless.

Frankly, I think there needs to be a widespread effort to open source education. Both content and assignments. There is no justification to charge tens of thousands in tuition and top this off with a few more thousand in jank software.