This guide is designed for counselors, teachers, and advisers who work with high school students from low-income families and students who are the first in their families to pursue a college education. It offers strategies for helping these students identify, consider, and enroll in “match” colleges — that is, selective colleges that are a good fit for students based on their academic profiles, financial considerations, and personal needs. Many of the suggestions in this guide are based on insights and lessons learned from the College Match Program, a pilot program that MDRC codeveloped with several partners and implemented in Chicago and New York City to address the problem of “undermatching,” or what happens when capable high school students enroll in colleges for which they are academically overqualified or do not apply to college at all.