While the existence of grade inflation in the American system of higher education is well documented, the argument that student entitlement drives this dynamic remains unproven. Drawing on an abductive analysis of twenty-nine in-depth, semi-structured interviews conducted by undergraduate co-authors, this study addresses these questions: (1) How do undergraduates on one elite campus understand the meaning and function of the grades they have received in college and (2) Do these students think that grading practices impact their undergraduate learning experience, and if so, how? Our results show that entitlement is not a fixed generational attitude so much as a conditional sentiment that individual professor’s grading practices can either disarm or inflame. Our study extends qualitative inquiry on students’ perceptions of grades and develops a student-centered “peer-to-peer” method that can be applied to a wide range of other issues in the sociology of higher education.