This brief draws on the data from interviews with counselors, 8th grade students, and parents, as well as observations of parent meetings, counselor meetings, assembly presentations and a day at the SDP High School Expo, collected in the 2008-09 school year at 10 K-8 and middle schools with varying student populations, Adequate Yearly Progress (AYP) statuses, and counselor approaches to the high school application process.The research presented in this brief builds on a regression analysis of high school applications and admissions for all district 8th graders. The analysis found that characteristics of the schools students attend in 8th grade helps to predict their likelihood of getting into a high school of their choice, even after controlling for their individual background characteristics and 7th grade record. Specifically, students who attended a K-8 school had higher odds of high school admission than their peers who attended a school with another grade span. And, students who attended smaller schools had higher odds of admission than their peers at larger schools. In other words, students with equal 7th grade records have unequal odds of high school admission, based on the type and size of the 8th grade school they attend. School type and size can also impact counselors’ ability to support their students. This brief presents a qualitative examination of the role of 8th grade counselors in the high school application process.