Solving problems through repeated attempts is a sequential modeling task: at each step, the solver receives feedback and decides how to revise their solutions. Predicting whether performance improves, plateaus, or regresses across attempts is central to understanding any iterative problem-solving process in both human learners and autonomous agents. Beyond outcomes, modeling what errors persist and how strategies shift across attempts provides deeper insight into the mechanics of sequential learning. Studying these dynamics requires observing many solvers as they attempt, receive feedback, and revise. Programming courses with automated grading provide this setting, as students iteratively submit code to test suites and receive feedback on every attempt. We therefore curate CodeInsight, a large-scale dataset of over 3 million submissions from 3,286 undergraduates across 2 introductory C++ courses in 2 academic years, with test-case-level outcomes, timestamps, and source code. On this dataset, we build a benchmark that evaluates models spanning parametric, sequential, and generative traditions under a shared calibration-and-scoring protocol, including a Recurrent State Space Model (RSSM) adapted to track solver characteristics through discrete latent variables and an LLM-based predictor that generates explicit solutions. The adapted RSSM achieves the strongest predictive accuracy on three of the four courses. The LLM predictor is less accurate but produces full submissions at each attempt, enabling direct analysis of failure modes. We find that the model’s coding proficiency is inversely related to predictive performance in this setting, with the LLM better understood as a generative solver conditioned on context rather than a faithful predictor of solver behavior. We publicly release our code and the dataset on request to facilitate future research.

Prediction of item difficulty from its text content is of substantial interest for automated generation of test items. In this paper, we focus on the related problem of recovering IRT-based difficulty when the data originally reported item p-value (percent correct responses). We model this item difficulty using a repository of reading passages and student data from US standardized tests from New York and Texas for grades 3-8 spanning the years 2018-23. This repository is annotated with meta-data on (1) linguistic features of the reading items, (2) test features of the passage, and (3) context features. Using a penalized regression model, we achieve an RMSE of 0.59 (compared to a 0.92 baseline) and a 0.77 correlation between true and predicted difficulty. We further evaluated the impact of LLM embeddings (ModernBERT, BERT, and LLaMA), finding that they marginally improve performance but function effectively as standalone alternatives to traditional linguistic features. Finally, we demonstrate how this difficulty prediction model powers a publicly available, human-in-the-loop tool for generating reading comprehension items.