That really doesn’t sound like much of an edge case to me. I’m willing to bet it’s a pretty typical workflow that people have if they own Apple devices.
If you stay in the "regular" apple workflow everything is fine: iphone camera -> icloud/photos (airdrop/photos) -> safari. If you deviate at certain points though the workflow breaks down. Whose fault is that?
You seriously over-estimate the "tech-savviness" of the average student and that really is part of the issue I'm pointing out here.
Source: I work in tech for higher ed.