While tired discourses surrounding Diversity, Equity, and Inclusion (DEI) have tended to limit themselves to those of inclusion, many students and faculty have adopted decolonization as a more relevant framework to question the embedded interests of higher education. As the university adapts to and appropriates these newer discourses, marginalized students are forced to navigate university structures while simultaneously working toward a decolonized future. “The Global Scholars Dilemma” demonstrates where the university currently lies in its attempts to appeal to communities of color while turning a blind eye to—and by extension refusing to detach from—the colonial dynamics which marginalize these very students. We are in conversation with la paperson’s A Third University Is Possible as a way to understand students and their roles within the larger decolonial movement. We explore the student experience in one intervention—the Global Scholars Program—focused on bringing together first-generation and underrepresented students interested in transnational education. Students interrogate concepts like global citizenship and its racialized and gendered aspects, as well as engaging with a cohort in a year-long program focused on identity, race, gender and decolonization. We write as a collective of four authors, two of whom participated in the program as students and two as faculty co-directors. We draw extensively on interviews with participants in the program, as well as the lived experiences of the authors. This chapter investigates the challenges faced by marginalized students in navigating university spaces not designed for them, and one attempt to undo some of those constraints.