One I recall from the early Mac era was the Kermit file transfer tool. [1] You'd run it on two computers. On one you'd tell it to SEND some file. Then on the other you'd type RECEIVE. A colleague of mine got absolutely fucking livid when he instead typed RECIEVE and it replied "I before E except after C".

He did have a point; the programmer obviously knew what was intended, but instead of just leaving it to a generic syntax error he went out of the way to have the computer be snotty. But the rage still seemed wildly disproportionate to me.

Years later, John Scalzi had a good way of putting it: "The failure mode of clever is asshole." [2]

[1] https://en.wikipedia.org/wiki/Kermit_(protocol) (I'm pretty sure it was this. It has been a while!)

[2] https://whatever.scalzi.com/2010/06/16/the-failure-state-of-...