ICML 2025

A Reasoning-Based Approach to Cryptic Crossword Clue Solving
Martin Andrews 1 Sam Witteveen 1
Abstract
Cryptic crossword clues are challenging language
tasks for which new test sets are released daily by
major newspapers on a global basis. Each cryptic
clue contains both the definition of the answer to
be placed in the crossword grid (in common with
regular crosswords), and ‘wordplay’ that proves
that the answer is correct (i.e. a human solver
can be confident that an answer is correct without
needing crossing words as confirmation). This
work describes an LLM-based reasoning system
built from open-licensed components that solves
cryptic clues by (i) hypothesising answers; (ii)
proposing wordplay explanations; and (iii) using
a verifier system that operates on codified reason-
ing steps. Overall, this system establishes a new
state-of-the-art performance on the challenging
Cryptonite dataset of clues from The Times and
The Telegraph newspapers in the UK. Because
each proved solution is expressed in Python, inter-
pretable wordplay reasoning for proven answers
is available for inspection.
1. Introduction
There has been significant work in reasoning in the fields
of mathematics (Jiang et al., 2023; Yang et al., 2023; Trinh
et al., 2024) and code generation (Ni et al., 2023; Ridnik
et al., 2024) which benefit from having strong verifiers to
validate their answers. This work tackles the relatively
under-studied reasoning task of cryptic crossword solving,
which has the following qualities:
• Thousands of people find Cryptic Crosswords a satisfy-
ing intellectual challenge on a daily basis. Solving these
puzzles requires understanding multi-layered language
constructs, blending logic, wordplay, and contextual nu-
ance. This provides a unique challenge for evaluating and
improving LLMs’ capabilities in NLU and reasoning.
1Red Dragon AI, Singapore. Correspondence to: Martin An-
drews <martin@reddragon.ai>.
Proceedings of the 42 nd International Conference on Machine
Learni...