This study used data on 1992 high school graduates from the National Education Longitudinal Study of 1988 (a survey that began with eighth graders in 1988 and followed them every two years through 1994) to examine the critical junctures when at-risk high school graduates are most likely to leave the pipeline to college enrollment, and to identify factors that increase their chances of successfully navigating the enrollment pipeline. An at-risk student was defined as having risk factors such as being from a single parent household, having an older sibling who dropped out of high school, and earning low grades between sixth and eighth grades. Highlights of the findings include: about 58 percent of graduates had one or more risk factors; of these, 30 percent successfully navigated the pipeline to college enrollment; at-risk students differed most from counterparts in their educational aspirations and academic preparation; and academically prepared at-risk students were much less likely than counterparts to take an entrance exam. After an introductory chapter, two chapters detail data and definitions and provide an overview of students at risk. The following two chapters present findings on the pipeline to a four-year college and compare at-risk students regarding completion of math courses, help received in the college application process, and level of school involvement of students, parents, and peers. Appended are a glossary, technical notes, and supplementary tables. (DB)