What Makes Cryptic Crosswords Challenging for LLMs?

Abdelrahman Sadallah, Daria Kotova, Ekaterina Kochmar


Abstract
Cryptic crosswords are puzzles that rely on general knowledge and the solver’s ability to manipulate language on different levels, dealing with various types of wordplay. Previous research suggests that solving such puzzles is challenging even for modern NLP models, including Large Language Models (LLMs). However, there is little to no research on the reasons for their poor performance on this task. In this paper, we establish the benchmark results for three popular LLMs: Gemma2, LLaMA3 and ChatGPT, showing that their performance on this task is still significantly below that of humans. We also investigate why these models struggle to achieve superior performance. We release our code and introduced datasets at https://github.com/bodasadallah/decrypting-crosswords.
Anthology ID:
2025.coling-main.342
Volume:
Proceedings of the 31st International Conference on Computational Linguistics
Month:
January
Year:
2025
Address:
Abu Dhabi, UAE
Editors:
Owen Rambow, Leo Wanner, Marianna Apidianaki, Hend Al-Khalifa, Barbara Di Eugenio, Steven Schockaert
Venue:
COLING
SIG:
Publisher:
Association for Computational Linguistics
Note:
Pages:
5102–5114
Language:
URL:
https://aclanthology.org/2025.coling-main.342/
DOI:
Bibkey:
Cite (ACL):
Abdelrahman Sadallah, Daria Kotova, and Ekaterina Kochmar. 2025. What Makes Cryptic Crosswords Challenging for LLMs?. In Proceedings of the 31st International Conference on Computational Linguistics, pages 5102–5114, Abu Dhabi, UAE. Association for Computational Linguistics.
Cite (Informal):
What Makes Cryptic Crosswords Challenging for LLMs? (Sadallah et al., COLING 2025)
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PDF:
https://aclanthology.org/2025.coling-main.342.pdf