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High-dosage tutoring accelerates student learning by approximately one-third of a grade level per year (Nickow et al., 2024), yet effective implementation at scale is often undermined by inadequate data systems. This study employs a multi-case, design-based approach to analyze how five state-led tutoring initiatives, collectively serving over 45,000 students across more than 300 schools, developed data infrastructures to monitor and evaluate policy implementation. Cross-case analysis yielded four key implementation insights: clearly established data-sharing protocols mitigate legal and technical barriers; streamlined reporting processes enhance data accuracy and usability; transparent performance monitoring strengthens accountability mechanisms; and integrating tutoring data with statewide education systems fosters sustainable impact. Findings provide actionable guidance for policymakers to translate tutoring investments into measurable improvements in outcomes.