To date, much of what is known about supporting children’s transition to kindergarten focuses on classroom-level practices implemented by early care and education (ECE) programs and kindergarten teachers, with little attention to the organizational conditions that support or hinder the implementation of those practices. This design options report focuses on Head Start and proposes two descriptive study designs to illuminate those systems-level supports and cross-system collaborations. The overall goal of these proposed studies is to better understand the landscape of those systems-level approaches and how they may be associated with positive kindergarten transitions for children attending Head Start and their families. (author abstract)