I worked in e-mail security for quite a while. "Write an e-mail address parser" was my go-to technical interview question.
It was pretty easy to see if the candidate had ever given any real thought to e-mail (most had not); and you could also pick up a lot of signals about engineering style, for instance if they started with a regex (fewer did than I expected). And it was trivial to adjust the difficulty: if someone thought the question was easy and had a fast solution, you could just throw them a test-case like the ones in this article.
(Note: the actual title is "Your E-Mail Validation Logic is Wrong" -- and it's only about addresses, the author isn't implying that e-mail systems can't validate messages nor for that matter addresses.)