Federal guidance allows Head Start grant recipients to apply to the Office of Head Start to shift funding (i.e., convert enrollment slots) from Head Start services for preschool-age children to Early Head Start services for pregnant women, infants, and toddlers. Yet scant information is available about how grant recipients navigate the conversion process, the challenges they face along the way, and factors or supports that facilitate the process. This report presents findings from six case studies of grant recipients that converted enrollment slots from Head Start to Early Head Start in 2021. In it we present research findings pertaining to the entire conversion process from start to finish, beginning with how grant recipient staff decided whether to convert enrollment slots through implementation of new or expanded Early Head Start services. We also describe how the conversion process differs for programs with different characteristics and contexts. We also present recommendations from study participants for improving the process of converting enrollment slots and implementing high-quality Early Head Start services.