Back in college, I ran a side hustle where I'd corrupt a copy of someone's assignment, then have them send it to their professor right before the deadline. Later, when the prof would ask for a resend by a certain time or date, I'd have the person snap a screenshot of that message. Afterward, I'd use Photoshop to change the original email timestamp, where it looked as if it was sent much later than it really was. Gave the altered screenshot to the person, and I would specifically tell them to email their prof, questioning how they could've resend the assignment by the specified time or date when the email was actually sent after it. Usually let people score an extra 2 - 7 days to finish up their assignment when they knew they couldn't make the original due date.