I always had to make judgement calls myself though. One guy did what on the surface seemed similar but wasn't. He was a goof as a student, always conning around for a handout --- the kind of person who, if he put into real life the effort he used trying to avoid it, he would have succeeded easily. He asked for an open-ended extension, and I said no. I later found out that he went out to California to join the professional bowlers tour, and never, to my knowledge came back to school. .... hope he was REAL good at it.
You don't win them all as an adult, and surely not as a teacher. Kinda painful much of the time. I had a bunch of Rap-group-gangstas show up at the office once trying to back some "student's" play to be let off some assignment because they had a gig. The student was already flunking soundly, gigs or not. I told the "gangstas" to clear-the-hell out of my corridor and doorway or I was calling campus police. They seemed to suddenly acquire their hearing facilities (apparently they weren't drummers) and scattered. Their leader came in to the office, was told the truths of life, didn't ever do the work, and dropped out.