Like every school across the country, Holyoke High School, in Holyoke, Massachusetts, struggled during remote learning: Teachers had to adjust to new technologies, and many students felt disconnected from the school environment. Despite these pandemic-induced challenges, Holyoke school leaders and staff kept student engagement at the forefront of their efforts to ensure continuity of learning. This profile of Holyoke from CRPE and the Christensen Institute details the school's practices that have proven successful, how they have adapted in the face of the pandemic, and how other school communities can begin conversations about adopting similar practices. School districts seeking to prioritize student engagement this school year can learn from Holyoke High School. Start by considering the following questions: (1) How can high schools help every student succeed by multiplying the number of pathways to graduation while maintaining high expectations? (2) What designs most effectively help each student feel known and supported by a caring adult, even in a large school environment? and (3) What existing structures in high schools are well-suited to be improved and expanded to meet students' and families' expectations?