From 2016 to 2021, the University of Connecticut Administrator Preparation Program (UCAPP) joined six other principal preparation programs across the country, inclusive of their district and state partners, to reshape the principal preparation programs under The Wallace Foundation’s University Principal Preparation Initiative (UPPI). This work began with a vision for program redesign focused on ensuring that all aspects of UCAPP would be more rigorous, coherent, and authentically connected to the work of a school leader. Therefore, a major shift for UCAPP in becoming more authentic was the development of four experience-based, formative assessments, grounded in the real work and responsibilities of school leaders. The UCAPP core assessments are project-based tasks that candidates complete to practice foundational principalship work and are used to measure their competencies in instructional leadership, talent management, and organizational leadership. The core assessment tasks allow candidates to practice authentic principalship work in schools as part of the clinical experience. Candidates also complete a school change capstone project.