This strange Windows koan, er... error message must've been designed by a zen master! Found at project x3150 [Flickr] - via Look at This ...
The weirdest computer error I've ever encountered was: "Bad magic number. Seek bloody revenge." (An old *nix computer in college way back when - I don't even remember what I was doing but I'll remember that error message till the day I die!).
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The Fieldata COBOL compiler for UNIVAC Exec 8 had a diagnostic that read:
Statement is vacuous.
Windows presents Choose Your Own Error! How exciting!
Also, the apparent tautology, "the filename exists or it doesn't" is false (though I am sure you are aware of that). The syntax of a rename command is usually rename filename1 filename2. When the error message says, "duplicate file name or file not found," it means that filename2 already exists or filename1 does not exist.
It's even funnier if you imagine a five year old voice reading it.
But how could they forget to include the incredible hulk?