Sandpiper: Orchestrated AI-Annotation for Educational Discourse at Scale

Digital educational environments are expanding toward complex AI and human discourse, providing researchers with an abundance of data that offers deep insights into learning and instructional processes. However, traditional qualitative analysis remains a labor-intensive bottleneck, severely limiting the scale at which this research can be conducted. We present Sandpiper, a mixed-initiative system designed to serve as a bridge between high-volume conversational data and human qualitative expertise. By tightly coupling interactive researcher dashboards with agentic Large Language Model (LLM) engines, the platform enables scalable analysis without sacrificing methodological rigor. Sandpiper addresses critical barriers to AI adoption in education by implementing context-aware, automated de-identification workflows supported by secure, university-housed infrastructure to ensure data privacy. Furthermore, the system employs schema-constrained orchestration to eliminate LLM hallucinations and enforces strict adherence to qualitative codebooks. An integrated evaluations engine allows for the continuous benchmarking of AI performance against human labels, fostering an iterative approach to model refinement and validation. We propose a user study to evaluate the system's efficacy in improving research efficiency, inter-rater reliability, and researcher trust in AI-assisted qualitative workflows.

Utility-Preserving De-Identification for Math Tutoring: Investigating Numeric Ambiguity in the MathEd-PII Benchmark Dataset

Large-scale sharing of dialogue-based data is instrumental for advancing the science of teaching and learning, yet rigorous de-identification remains a major barrier. In mathematics tutoring transcripts, numeric expressions frequently resemble structured identifiers (e.g., dates or IDs), leading generic Personally Identifiable Information (PII) detection systems to over-redact core instructional content and reduce dataset utility. This work asks how PII can be detected in math tutoring transcripts while preserving their educational utility. To address this challenge, we investigate the "numeric ambiguity" problem and introduce MathEd-PII, the first benchmark dataset for PII detection in math tutoring dialogues, created through a human-in-the-loop LLM workflow that audits upstream redactions and generates privacy-preserving surrogates. The dataset contains 1,000 tutoring sessions (115,620 messages; 769,628 tokens) with validated PII annotations. Using a density-based segmentation method, we show that false PII redactions are disproportionately concentrated in math-dense regions, confirming numeric ambiguity as a key failure mode. We then compare four detection strategies: a Presidio baseline and LLM-based approaches with basic, math-aware, and segment-aware prompting. Math-aware prompting substantially improves performance over the baseline (F1: 0.821 vs. 0.379) while reducing numeric false positives, demonstrating that de-identification must incorporate domain context to preserve analytic utility. This work provides both a new benchmark and evidence that utility-preserving de-identification for tutoring data requires domain-aware modeling.

AI Annotation Orchestration: Evaluating LLM verifiers to Improve the Quality of LLM Annotations in Learning Analytics

Large Language Models (LLMs) are increasingly used to annotate learning interactions, yet concerns about reliability limit their utility. We test whether verification-oriented orchestration-prompting models to check their own labels (self-verification) or audit one another (cross-verification)-improves qualitative coding of tutoring discourse. Using transcripts from 30 one-to-one math sessions, we compare three production LLMs (GPT, Claude, Gemini) under three conditions: unverified annotation, self-verification, and cross-verification across all orchestration configurations. Outputs are benchmarked against a blinded, disagreement-focused human adjudication using Cohen's kappa. Overall, orchestration yields a 58 percent improvement in kappa. Self-verification nearly doubles agreement relative to unverified baselines, with the largest gains for challenging tutor moves. Cross-verification achieves a 37 percent improvement on average, with pair- and construct-dependent effects: some verifier-annotator pairs exceed self-verification, while others reduce alignment, reflecting differences in verifier strictness. We contribute: (1) a flexible orchestration framework instantiating control, self-, and cross-verification; (2) an empirical comparison across frontier LLMs on authentic tutoring data with blinded human "gold" labels; and (3) a concise notation, verifier(annotator) (e.g., Gemini(GPT) or Claude(Claude)), to standardize reporting and make directional effects explicit for replication. Results position verification as a principled design lever for reliable, scalable LLM-assisted annotation in Learning Analytics.