This document presents case studies from the qualitative study [see ED500519], each of which highlights a student who struggled at a different point in the postsecondary planning process. These case studies draw on a longitudinal, qualitative study of 105 CPS students in three high schools. They are based on five student interviews conducted between spring of these students' junior year of high school (March 2005) and their graduation the following year (June 2006) and represent common themes that emerged from the qualitative work. (Contains 20 endnotes.) [For the executive summary of the full report, see ED500677.] [Karen Roddie, Jamiliyah Gilliam, and Desmond Patton contributed to this report.]