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Gizmodo·4 min read·medium

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

T
Tom Hawking
I Gave the Hardest Cryptic Crossword I Could Find to a Bunch of LLMs
✦AI Summary

A journalist tests the capabilities of modern Large Language Models by challenging them to solve a notoriously difficult Australian cryptic crossword. The article explores whether AI can replicate the human-like creative perversity required for complex wordplay.

Why it matters

It highlights the evolving boundaries of AI reasoning and its ability to handle linguistic nuance and cultural context in non-standard tasks.

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So this morning I woke to the news that Firefox would be adding a daily AI-powered crossword to its ever more cluttered content-rich new tab page. This is all well and good, but it also got me thinking about something. I love a good cryptic crossword, and… well, if there’s one form of crossword with which surely AI would struggle, it’s that most perverse and curiously human of puzzles, the cryptic crossword.

I bet that none of the consumer LLMs could make any sort of fist of tackling a proper cryptic. Right? Well, it seems that I’m not the only one thinking about this—and it also turns out that perhaps I’m wrong.

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