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. Each section of the report suggests tools and resources in the form of websites and printed materials that counselors, advisers, and students can use, as well as case studies to illustrate the experiences of "College Match" participants throughout the process. An appendix contains a comprehensive list of online tools and resources. [Additional funding for the College Match Program was provided by The Heckscher Foundation for Children.]