I accidentally typed "git gud" one time and Steam notified that I have completed all achievements of Dark Souls 1-3 at the same time (I don't even own the games)
In one notorious incident, Warren added a DWIM feature to the command interpreter used at Xerox PARC. One day another hacker there typed delete *$ to free up some disk space. (The editor there named backup files by appending $ to the original file name, so he was trying to delete any backup files left over from old editing sessions.) It happened that there weren't any editor backup files, so DWIM helpfully reported *$ not found, assuming you meant 'delete *'. It then started to delete all the files on the disk!