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Re:Students are failing AP tests because the College Board c... by askvictor on Thursday May 21, 2020 @10:51PM (#23268244)
That might be part of the problem, though other comments also point out that students were copying file to a computer, then changing file extension, then uploading. Possibly this was as a result of the iOS browser rejecting the file in the first place due to the shoddy input filtering mentioned.

But going a bit bigger picture, the problem is that we still use file extensions to denote file type.

Re:Students are failing AP tests because the College Board c... by Wowfunhappy on Thursday May 21, 2020 @11:16PM (#23268346)
This keeps getting brought up because there was one anecdote in the Verge story about a student who renamed the file on their computer. (Which still shouldn't have caused the test to keel over, but it's at least slightly more understandable.)

However, there were many other reports of students going the more "normal" route of just uploading through their iPhones, which caused the website to outright hang.