Why does it matter? If I'm doing a Puzzle Hunt, and I give it a few cryptics to help me with, and it gets half of them right (cryptics are generally easy to verify after you get the solution), then it did what I needed it for.
It's impressive how computer technology keeps making puzzle hunt construction get harder. Like how much a search engine or Wikipedia helps with the original Mystery Hunts
oh absolutely, you have things like /r/PictureGame who have perfected the art of fooling reverse image search. Meanwhile many world puzzles put specific tricks to fool Nutrimatic, or anagrams that can't be easily brute forced. It is definitely an arms race.