This article examines the extent to which indicators of the college-going climate of urban high schools are associated with students' application to, enrollment in, and choice among four-year colleges. The investigators examine two mechanisms by which high schools may shape college enrollment among low-income students in an urban school system: (1) by ensuring whether seniors who aspire to a four-year college degree take the steps to apply to and enroll in a four-year college, and (2) by influencing whether students enroll in colleges with selectivity levels at or above the kinds of colleges they are qualified to attend (a "college match"). We investigate different approaches to measuring college-going climate and develop new indicators. Findings suggest that qualifications and college aspirations will not necessarily translate into four-year college enrollment if urban high schools do not develop organizational norms and structures that guide students effectively through the college application process. Urban students who attend high schools where there is a pattern of four-year college-going, where teachers report high expectations and strong supports for college attendance, and where there is high participation in financial aid application are more likely to plan to attend, apply to, be accepted into, and enroll in a four-year college that matches their qualifications. (Contains 12 notes, 6 tables, and 1 figure.)