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Applied AI·July 28, 2026·1 min read

I Gave the Hardest Cryptic Crossword I Could Find to a Bunch of LLMs

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LLMs struggling with the hardest cryptic crosswords is a narrow but clear example of where current models still miss layered, culture-heavy reasoning. Use this as a calibration point — they’re powerful pattern machines, but for tasks that hinge on deep shared context and misdirection, keep humans in the loop.