Background: Advising students on the transition from high school to college is a central part of school counselors' professional responsibility. The American School Counselor Association recommends a school counselor caseload of 250 students; however, prior work yields inconclusive evidence on the relationship between school counseling and school-level counseling resources and students' college trajectories. Focus of Study:This study evaluates the relationship between access to school counselors and several critical indicators of student transitions between high school and college. Research Design: The study utilizes the Education Longitudinal Study of 2002 to explore the relationships between the school counselor caseload and students' progress throughout the high school-to-college pipeline. The key indicator is the counselor caseload for students at a given high school, measured as the number of 10th graders per counselor at the high school at which each student is enrolled. The outcome variables are students' college expectations, whether students spoke with a counselor about college, taking the SAT, and college enrollment. Logistic and multinomial logistic regression analyses are applied to examine the relationships between these variables. Findings: Students in schools with small counselor caseloads enjoy greater success at navigating the high school-to-college pipeline. Controlling for student- and school-level characteristics, students in schools where counselors are responsible for advising a large number of students are less likely to speak with a counselor about college, plan to attend college, take the SAT, and enroll in a 4-year college. Conclusions: The findings support the claim that a smaller school counselor caseload may increase students' access to key college preparation resources and raise 4-year college enrollment rates.