The Riddle Riddle: Testing Flexible Reasoning in Large Language Models and Humans
On the map: LLM reasoning → Reasoning benchmarks and evaluation
Abstract (arXiv)
Humans flexibly adapt their reasoning strategies to the requirements of a given problem. Large language models (LLMs) have performed well on many cognitive tasks, however, it is unclear whether this accuracy is a result of pattern matching from training data or flexible reasoning. Here, we introduce a novel paradigm to test this question: the riddle riddle paradigm. Riddle riddles are word problems written to mimic popular riddles, but altered so their answers only require literal interpretations. Identifying correct answers requires looking past the structure of each question and flexibly apply different reasoning strategies based on the content. If LLMs respond to surface features, such as form, a riddle-like structure should cause models to use an inventive reasoning strategy even when a literal interpretation suffices. Alternatively, if LLMs reason based on content, they should flexibly switch strategies when appropriate. Across two experiments with nine state-of-the-art LLMs and 100 human participants, we show humans and LLMs fail on this paradigm in opposite directions. LLMs were far more accurate on genuine riddles than on riddle riddles (84.9% vs. 50.7%); whereas humans showed the reverse effect (50.5% vs. 80.5%). Error analysis shows that 90.8% of LLM errors on riddle riddles (the condition where they show diminished performance) were due to inappropriate use of inventive reasoning while only 57.6% of human errors on genuine riddles were due to overextending literal reasoning. Thus, while both groups make mistakes, reasoning mistakes are made more often by LLMs than by humans. Overall, LLMs' strong performance on genuine riddles may reflect memory retrieval rather than flexible strategy selection, and without stimuli designed to elicit this contrast, it becomes easy to conflate LLM-generated outputs that look like reasoning with genuine reasoning.
Key facts. No citing papers in the map yet (data through 7 Oct 2026). Placed in Reasoning benchmarks and evaluation, one of 17 directions in LLM reasoning. Builds on 13 of its 25 references that are in the map. First posted on arXiv 25 Jun 2026.
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- 2023Sparks of Artificial General Intelligence: Early experiments with GPT-4cited by 2,579
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- 2019Right for the Wrong Reasons: Diagnosing Syntactic Heuristics in Natural Language Inferencecited by 864
- 2023Quantifying Language Models' Sensitivity to Spurious Features in Prompt Design or: How I learned to start worrying about prompt formattingcited by 778
- 2023The Reversal Curse: LLMs trained on "A is B" fail to learn "B is A"cited by 399
- 2022Using cognitive psychology to understand GPT-3cited by 389
- 2025Reasoning or Memorization? Unreliable Results of Reinforcement Learning Due to Data Contaminationcited by 81
- 2024The Illusion-Illusion: Vision Language Models See Illusions Where There Are Nonecited by 14
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- 2025RiddleBench: A New Generative Reasoning Benchmark for LLMs
- 2024RISCORE: Enhancing In-Context Riddle Solving in Language Models through Context-Reconstructed Example Augmentation
- 2025The Metacognitive Bottleneck: Japanese Riddles Reveal Fundamental Limits of Machine Insight and Self-Evaluation in Reasoning AI
- 2025EnigmaEval: A Benchmark of Long Multimodal Reasoning Challenges
- 2025Reasoning Strategies in Large Language Models: Can They Follow, Prefer, and Optimize?