Math Education Digital Shadows for facilitating learning with LLMs: Math performance, anxiety and confidence in simulated students and AIs

While Large Language Models (LLMs) have achieved near-perfect performance in \emph{solving} high-school mathematics, their ability to \emph{evaluate} the diverse reasoning processes of real human students remains under-examined. To bridge this gap, we introduce \textbf{RealMath-Eval}, a rigorously annotated benchmark of 224 real-world exam responses from high schools. Our initial evaluation reveals that even state-of-the-art LLM judges struggle significantly on this task, exhibiting a high Mean Squared Error ($\sim$2.96) against expert human grading. To probe a plausible explanation, we contrast this performance with a control setting where the same judges evaluate synthetic LLM-generated solutions. We identify a stark Evaluation Gap'': judges are considerably more accurate and consistent on synthetic text (MSE $\sim$1.17) but struggle to generalize to authentic student reasoning. Through semantic embedding analysis, we find that synthetic errors suffer from a structural collapse'' into predictable, low-dimensional linear subspaces, whereas human errors form a more diverse error space. Furthermore, generative probability probes suggest that human reasoning involves significantly higher information-theoretic surprisal, indicating that student reasoning transitions are more out-of-distribution for current models. Finally, we find that surface-level style transfer fails to close this gap. Our findings suggest that current LLM evaluation pipelines relying heavily on synthetic data may not adequately capture the diversity of authentic student mathematical reasoning.

Despite the pivotal role of numerical reasoning as the cornerstone of mathematical capabilities in large language models (LLMs) across applications, few benchmarks evaluate LLMs by integrating numerical processing and mathematical reasoning, hindering the interpretability of failures in math tasks. We introduce PyraMathBench, a comprehensive hierarchical benchmark with 32,505 questions derived from 7,404 math word problems, spanning 4 key cognitive aspects, 14 subcategories, and 2 modalities. Experiments reveal that LLMs' performance is severely compromised by inadequate numerical computation and weak handling of abstract numerical questions. To address this, we propose the Smart Optimization & Learning-based VErsatile module (SOLVE) and Interactive Relative Policy Optimization (IRPO), which enhance LLMs' numerical-mathematical synergy via efficient tool calls (fuzzy matching and low-quality call rejection). Comparative experiments show Qwen-2.5 achieves a 5.0 score improvement with SOLVE and IRPO training.

Following the recent achievement of gold-medal performance on the IMO by frontier LLMs, the community is searching for the next meaningful and challenging target for measuring LLM reasoning. Whereas olympiad-style problems measure step-by-step reasoning alone, research-level problems use such reasoning to advance the frontier of mathematical knowledge itself, emerging as a compelling alternative. Yet research-level math benchmarks remain scarce because such problems are difficult to source (e.g., Riemann Bench and FrontierMath-Tier 4 contain 25 and 50 problems, respectively). To support reliable evaluation of next-generation frontier models, we introduce Soohak, a 439-problem benchmark newly authored from scratch by 64 mathematicians. Soohak comprises two subsets. On the Challenge subset, frontier models including Gemini-3-Pro, GPT-5, and Claude-Opus-4.5 reach 30.4%, 26.4%, and 10.4% respectively, leaving substantial headroom, while leading open-weight models such as Qwen3-235B, GPT-OSS-120B, and Kimi-2.5 remain below 15%. Notably, beyond standard problem solving, Soohak introduces a refusal subset that probes a capability intrinsic to research mathematics: recognizing ill-posed problems and pausing rather than producing confident but unjustified answers. On this subset, no model exceeds 50%, identifying refusal as a new optimization target that current models do not directly address. To prevent contamination, the dataset will be publicly released in late 2026, with model evaluations available upon request in the interim.