The context and variables that affect at-risk students are constantly changing. It is imperative that school counselors understand the risk factors for students and the cultural and social contexts the individual lives within. Working with at-risk students is even more challenging with the millennial generation. The culture in this generation promotes instant gratification as society has reinforced that all individuals will succeed. At-risk students in this generation can be in disbelief of even being at-risk and may assume that others will solve their problems. Federally funded TRIO programs have shown to a positive impact on at-risk student development. Although there has been sufficient evaluation and review of TRIO programs' impact on disadvantaged college students, there is a lack of research of student evaluation of their high school counselors after they graduate. It is important to consider the high school counselor's impact on postsecondary success. College students involved in TRIO completed surveys rating their high school counselor. School counselor rating scores were correlated with the number of school counselors in that school, r(20) = 0.45, p = 0.043. This study has implications for school counselors and emphasizes the importance of school counselor contact. This research is the first step in the evaluation of high school counselors from students even when they are no longer high school students. Key take away points: (1) At-risk students from schools where school counselors had smaller caseloads rated their counselors more favorably based on the ASCA National Model; (2) Students who worked rated school counselors as more effective suggests that characteristics of students who work has a positive impact on their relationship with school counselor; and (3) This study is a first step in understanding school counselor effectiveness, especially for at-risk youth involved in a TRIO college program.