# DeepQuestion: Systematic Generation of Real-World Challenges for Evaluating LLMs Performance

arXiv: https://arxiv.org/abs/2505.24532 · HTML: https://mlsanity.com/paper/2505.24532/

## Key facts

- No citing papers in the map yet (data through 14 Oct 2026).
- Builds on 13 of its 24 references that are in the map.
- First posted on arXiv 30 May 2025.

## Builds on (most cited first, 13 of 13)

- [GPT-4 Technical Report](https://mlsanity.com/paper/2303.08774/) (2023)
- [The Llama 3 Herd of Models](https://mlsanity.com/paper/2407.21783/) (2024)
- [Training Verifiers to Solve Math Word Problems](https://mlsanity.com/paper/2110.14168/) (2021)
- [Qwen3 Technical Report](https://mlsanity.com/paper/2505.09388/) (2025)
- [Measuring Mathematical Problem Solving With the MATH Dataset](https://mlsanity.com/paper/2103.03874/) (2021)
- [GPQA: A Graduate-Level Google-Proof Q&A Benchmark](https://mlsanity.com/paper/2311.12022/) (2023)
- [MMLU-Pro: A More Robust and Challenging Multi-Task Language Understanding Benchmark](https://mlsanity.com/paper/2406.01574/) (2024)
- [Gemma 3 Technical Report](https://mlsanity.com/paper/2503.19786/) (2025)
- [Phi-4 Technical Report](https://mlsanity.com/paper/2412.08905/) (2024)
- [GSM-Symbolic: Understanding the Limitations of Mathematical Reasoning in Large Language Models](https://mlsanity.com/paper/2410.05229/) (2024)
- [Open-LLM-Leaderboard: From Multi-choice to Open-style Questions for LLMs Evaluation, Benchmark, and Arena](https://mlsanity.com/paper/2406.07545/) (2024)
- [Proof or Bluff? Evaluating LLMs on 2025 USA Math Olympiad](https://mlsanity.com/paper/2503.21934/) (2025)
- [Medical Large Language Model Benchmarks Should Prioritize Construct Validity](https://mlsanity.com/paper/2503.10694/) (2025)

## Abstract (arXiv)

While Large Language Models (LLMs) achieve near-human performance on standard benchmarks, their capabilities often fail to generalize to complex, real-world problems. To bridge this gap, we introduce DeepQuestion, a scalable, automated framework that systematically elevates the cognitive complexity of existing datasets. Grounded in Bloom's taxonomy, DeepQuestion generates (1) scenario-based problems to test the application of knowledge in noisy, realistic contexts, and (2) instruction-based prompts that require models to create new questions from a given solution path, assessing synthesis and evaluation skills. Our extensive evaluation across ten leading open-source and proprietary models reveals a stark performance decline with accuracy dropping by up to 70% as tasks ascend the cognitive hierarchy. These findings underscore that current benchmarks overestimate true reasoning abilities and highlight the critical need for cognitively diverse evaluations to guide future LLM development.