ChatGPT vs a cryptic crossword

ChatGPT vs a cryptic crossword

The first Times crossword

The first Times crossword

Having seen several mind-blowing articles about ChatGPT’s ability (most notably this one), I wondered how ChatGPT would fare solving a cryptic crossword.

I decided to try with an easy one: a Quick Cryptic from The Times. I had a search through the Times for the Times archives to try and find one on the easier side. Eventually, I settled on Quick Cryptic 2273 by Beck, which was described as “very gentle” by the solver.


Okay, let’s get started:

A swing… and a miss. Wrong answer, and the reasoning is nonsensical.

(The answer is “MANTRA” – MAN (chap) and ART (skill) reversed (recalled)).


Let’s hit “try again”:

Correct answer! But let’s check the reasoning…

Chap is indeed derived from chapman (which was news to me), and a chapman is a trader.

But that’s where we start to go off the rails… TRADER reversed is REDART, not REDARAT. And REDARAT is definitely not a homophone of MANTRA.


One more try:

Okay – again, the right answer! How is it getting to the answer though?

taking the first letter of the word “chap” (M)

uhhh…

the past tense of the verb “to recall” (ANT)

umm…

and the first two letters of the word “skill” (RA)

???


Okay, let’s try another clue.

The solution here is IMPACT – ACT (legislation) after I (one) and MP (politician) (“Introduced by” is an indicator to put the I MP at the front.)


Maybe the clues I’ve been trying have been too hard. Let’s try the easiest one I can find.

So close, yet so far… The reasoning is almost right. The correct reasoning is S + US (American) + HI (greeting).


Conclusion

Credit where it’s due, ChatGPT gets a couple of things right in these tests:

  • it understands the structure of a clue in most case: it gets that the clue is formed of a straight and cryptic part, and the straight part is at the start or end
  • it generally answers with the correct amount of letters
  • it understands what wordplay is (anagrams, homophones, reversal, concatenation, etc.), and kind of applies them – just incorrectly

And, importantly, it occasionally gets to the correct answer. But in these cases, it appears to reach the correct answer entirely based on the straight clue: it forces the cryptic solution backwards from there (even when it makes no sense).

I find it interesting that it replies with 100% confidence, despite the reasoning being obviously (to a human) absurd.

I guess cryptic crosswords fall into the (surprisingly small) category of things that ChatGPT just isn’t very good at!

James Williams • 2025