In this case, 10 Latina/o high school seniors and one high school counselor share their perspectives on how college information and opportunities are distributed in their school. In doing so, it becomes evident that efforts are not systematic or equitable. As a result, dilemmas arise when some students are denied the opportunity to attend a college fair held off campus during the school day and find alternative means of doing so. Current and aspiring educational leaders are urged to consider the ethical, safety, and policy issues related to the immediate dilemmas and the larger concern regarding the school's college-going culture.