The College Bound Scholarship (CBS) is designed to inspire and encourage Washington middle school students from low-income families to prepare for and pursue postsecondary education. Postsecondary enrollment rates of College Bound students match or exceed those of non-College Bound Washington high school graduates; however, the postsecondary enrollment rate of College Bound students has fallen as the percentage of 7th and 8th grade students signing the pledge has increased. This study, funded by the Bill and Melinda Gates Foundation, provides a first look into eligible students' perceived obstacles to postsecondary enrollment, despite access to the College Bound scholarship. The authors do not present statistically significant results or tests among schools' programming. Rather, this study explores possible gaps in information and students' perceived obstacles to continuing education. This report begins with state program information and data from the Washington Student Achievement Council showing sign-up rates and postsecondary enrollment rates for students in public K-12 schools. Next, the authors present findings from: (1) Two focus groups of current seniors; (2) One survey of current seniors; and (3) One survey of recently graduated College Bound-eligible students designed to probe students' understanding of the College Bound program and their perceived obstacles to postsecondary enrollment. The authors conclude with recommendations for improving CBS postsecondary enrollment rates and suggest further research based on our findings. The following are appended: (1) Focus Group Instrument; (2) Participating Schools; (3) Methodology for Survey of Current Seniors; (4) Survey Instrument for Current Seniors; and (5) Invitation to Recent eligible low-income High School Graduates.