Accurate estimation of item (question or task) difficulty is critical for educational assessment but suffers from the cold start problem. While Large Language Models demonstrate superhuman problem-solving capabilities, it remains an open question whether they can perceive the cognitive struggles of human learners. In this work, we present a large-scale empirical analysis of Human-AI Difficulty Alignment for over 20 models across diverse domains such as medical knowledge and mathematical reasoning. Our findings reveal a systematic misalignment where scaling up model size is not reliably helpful; instead of aligning with humans, models converge toward a shared machine consensus. We observe that high performance often impedes accurate difficulty estimation, as models struggle to simulate the capability limitations of students even when being explicitly prompted to adopt specific proficiency levels. Furthermore, we identify a critical lack of introspection, as models fail to predict their own limitations. These results suggest that general problem-solving capability does not imply an understanding of human cognitive struggles, highlighting the challenge of using current models for automated difficulty prediction.

Large language models (LLMs) still lack delicate controllability over their responses, which is critical to enhancing their performance and the user experience. However, curating supervised fine-tuning (SFT) datasets to improve LLM controllability usually relies on human experts or proprietary LLMs, which requires additional costs. To bridge this gap, we propose Rule-based Data Recycling (RuleR), a data augmentation method incorporating multiple constraints into the original data samples according to predefined rules, which creates new training tasks to consolidate the controllability of LLMs. Instead of creating new data from scratch, RuleR “recycles” existing data by simply applying rule-based edits to their responses and appending the rule-instructions in their original instructions. Experimental results demonstrate RuleR’s effectiveness in improving LLM controllability while maintaining general instruction-following capabilities.