Bridges Institute is a small public urban high school founded in 1994 as part of the restructuring of a failing comprehensive high school. Part of a network of "critical" small schools in New York City, Bridges aims to interrupt the educational neglect of their students through carefully designed student-centered instruction and authentic assessment, as well as through active engagement in relevant social issues. While the school has experienced success at helping students "beat the odds," a previous study hinted that students faced considerable challenges in pursuing college degrees. The present study explores the issue more fully through an explicit examination of the college experiences of a group of Bridges alumni. Their perspectives on the challenges they faced, along with possible areas for action and further study, are discussed.