Every fall, eighth graders in the School District of Philadelphia (SDP) have the opportunity to apply to up to five district-managed high schools. The high school application system presents students and families with choices, but taking full advantage of the system requires understanding the high school admission criteria, the various programs and features of the district's 60 high schools and 24 charter high schools, and the steps in the application process. School choice research tends to focus on parent management of decisions, but this brief recognizes the critical role of students in managing the high school application process, particularly for adolescents from immigrant families whose parents are not familiar with the American educational system, do not speak English, and/or have limited education. This brief draws on interviews conducted with 47 eighth grade students and 27 parents during the 2008-09 school year, including 25 students from immigrant families and 16 immigrant parents. It also draws on interviews conducted with 10 counselors in elementary and middle schools about the high school application process. This brief describes how immigrant children and children of immigrants navigate the high school application process, reveals challenges specific to this group, and presents recommendations for schools and community organizations to better support these students. Challenges and Recommendations At-a-Glance are appended. (Contains 2 figures and 10 footnotes.)