This research is a collection of comparative case studies that examine the perspectives of four principals in their 1st year of implementing the High School College Collaborative (HSCC), which works to provide traditionally underserved high school students with the opportunity to receive college credit, possibly an associate of arts degree, concurrently with their high school diploma. In this research, we address the following questions: (a) What are the principals' experiences with implementing HSCC? (b) What are the specific challenges these principals face? and (c) How did the principals negotiate these challenges? This study aims to broaden perspectives on the requirements of school change work, thus increasing both principals' effectiveness and learning opportunities for all students.