This book explores the design and implementation of effective supplementary education programs that best prepare students for post-secondary life. Drawing from research and best practice in the fields of supplementary and afterschool education, youth development, and school–college–community partnerships, this book outlines a balanced approach to viewing supplementary education and community-based programs, which when designed alongside classroom learning, can meet the needs of underserved youth. This book challenges aspiring educational leaders to confront the traditional approach to curriculum as the sole purview of the classroom and instead positions supplementary education as a tool to improve schools and student success. Chapters discuss designing, implementing, and sustaining supplementary education programs that positively impact the social, emotional, and academic development of secondary school students, as well as effective strategies for developing stronger connections with the community. This text is designed for use in graduate preparation programs in educational leadership and includes pedagogical features such as learning objectives, reflective exercises, portfolio-building activities, and alignment to educational leadership standards.