When many of today's parents were students, the process of applying and enrolling in school was fairly simple and involved few choices. In many cases, a family visited the neighborhood public school at the start of the school year and enrolled the child at the school's office. But now, the proliferation of school-choice policies in districts across the country is turning school selection and enrollment as early as kindergarten into a multistep process that begins long before the school year begins. The confusion associated with this complex process can result in dissatisfaction with and a lack of engagement in the school system among parents. This brief describes lower-than-intended application rates to kindergarten in New York City, as well as differences in those application rates among different types of families and communities. An analysis of application and enrollment data for New York City public school students entering kindergarten for the 2016-2017 school year shows the extent to which families miss application opportunities at the starting gate to the largest school district in the United States. Furthermore, the analysis shows that some communities and populations miss these opportunities more than others. This brief describes the patterns identified in New York City and in so doing provides a model for how other school systems could use their application and enrollment data to improve their processes and outreach. [This report was written with Michelle Dixon, Margaret Hennessy, Vianny Lugo-Aracena, and Jed Teres.]