The case illuminates an academic advising session between an overworked academic advisor and a first-generation college student on the verge of dropping out of college due to financial and family concerns. The case highlights the informal leadership role advisors have in working with students and the ethical dilemmas they face in balancing institutional pressure and time demands with the advising needs of their students. Drawing upon social capital theory and servant leadership, the reader is asked to analyze the case and determine whether or not the actions of the academic advisor exhibit the qualities of servant leadership and are in the best interest of the student.